Abstract
Recent advances from our group in the design and applications of multimetallic bifunctional asymmetric catalysts are described. Suitable design of chiral ligands and selection of metals were important to realize cooperative bimetallic catalysis. In this account, our strategies for constructing flexible and diverse chiral environments in multimetallic complexes for the rapid optimization of targeted reactions, such as tertiary nitroaldol kinetic resolution, cyclopropanation of electron-deficient olefins, cyano-ethoxycarbonylation of aldehydes, direct Mannich-type reactions, the nitro-Mannich reaction, the anti -selective nitroaldol reaction, and amination, are discussed in detail.
1 Introduction
2 Heterobimetallic Rare-Earth-Alkali Metal-BINOL Complexes
2.1 Background
2.2 Catalytic Kinetic Resolution of Tertiary Nitroaldols
2.3 Catalytic Asymmetric Cyclopropanation of Enones
2.4 Catalytic Asymmetric Cyano-ethoxycarbonylation
3 La Aryloxide/Li Aryloxide/pybox Complexes for Direct Catalytic Asymmetric Mannich-type Reactions
4 Heterobimetallic Transition Metal/Rare-Earth Metal/Dinucleating Schiff Base Complexes
4.1 syn -Selective Nitro-Mannich-type Reaction
4.2 anti -Selective Nitroaldol Reaction
5 Homobimetallic Nickel/Dinucleating Schiff Base Complex
6 Rare-Earth Metal/Amide Complexes for Catalytic Asymmetric Amination
7 Summary
Key words
asymmetric catalysis - asymmetric synthesis - bifunctional catalysis - rare-earth metals - Lewis acids
References
1a New Frontiers in Asymmetric Catalysis
Mikami K.
Lautens M.
Wiley & Sons;
Hoboken NJ:
2007.
1b Comprehensive Asymmetric Catalysis
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
1999.
1c Comprehensive Asymmetric Catalysis
Suppl. 1:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
2003.
2 Machajewski TD.
Wang C.-H.
Angew. Chem. Int. Ed.
2000,
39:
1352
3a Kanai M.
Kato N.
Ichikawa E.
Shibasaki M.
Synlett
2005,
1491
3b Shibasaki M.
Kanai M.
Matsunaga S.
Aldrichimica Acta
2006,
39:
31
3c Shibasaki M.
Matsunaga S.
Chem. Soc. Rev.
2006,
35:
269
3d Shibasaki M.
Kanai M.
Org. Biomol. Chem.
2007,
5:
2027
3e Matsunaga S.
Shibasaki M.
Bull. Chem. Soc. Jpn.
2008,
81:
60
4a Yamamoto H.
Futatsugi K.
Angew. Chem. Int. Ed.
2005,
44:
1924
4b Ma J.-A.
Cahard D.
Angew. Chem. Int. Ed.
2004,
43:
4566
4c Multimetallic Catalysis in Organic Synthesis
Shibasaki M.
Yamamoto Y.
Wiley-VCH;
New York:
2004.
5a Dalko PI.
Moisan L.
Angew. Chem. Int. Ed.
2004,
43:
5138
5b
5c Berkessel A.
Gröger H.
Asymmetric Organocatalysis
Wiley-VCH;
New York:
2005.
5d Taylor MS.
Jacobsen EN.
Angew. Chem. Int. Ed.
2006,
45:
1520
5e Marcelli T.
van Maarseveen JH.
Hiemstra H.
Angew. Chem. Int. Ed.
2006,
45:
7496
5f Connon SJ.
Chem. Eur. J.
2006,
12:
5418
5g Lelais G.
MacMillan DWC.
Aldrichimica Acta
2006,
39:
79
5h Enders D.
Grondal C.
Hüttl MRM.
Angew. Chem. Int. Ed.
2007,
46:
1570
5i Barbas CF.
Angew. Chem. Int. Ed.
2008,
47:
42
5j Enantioselective Organocatalysis, Reactions and Experimental Procedures
Dalko PI.
Wiley-VCH;
Weinheim:
2007.
6a Sasai H.
Arai T.
Satow Y.
Houk KN.
Shibasaki M.
J. Am. Chem. Soc.
1995,
117:
6194 ; and references cited therein
6b Sasai H.
Suzuki T.
Itoh N.
Tanaka K.
Date T.
Okamura K.
Shibasaki M.
J. Am. Chem. Soc.
1993,
115:
10372
7a Shibasaki M.
Sasai H.
Arai T.
Angew. Chem., Int. Ed. Engl.
1997,
36:
1236
7b Shibasaki M.
Yoshikawa N.
Chem. Rev.
2002,
102:
2187
8a Aspinall HC.
Chem. Rev.
2002,
102:
1807
8b Aspinall HC.
Dwyer JLM.
Greeves N.
Steiner A.
Organometallics
1999,
18:
1366
8c Aspinall HC.
Bickley JF.
Dwyer JLM.
Greeves N.
Kelly RV.
Steiner A.
Organometallics
2000,
19:
5416
8d Di Bari L.
Lelli M.
Pintacuda G.
Pescitelli G.
Marchetti F.
Salvadori P.
J. Am. Chem. Soc.
2003,
125:
5549
8e Wooten AJ.
Carroll PJ.
Walsh PJ.
Angew. Chem. Int. Ed.
2006,
45:
2549
9a Yoshikawa N.
Yamada YMA.
Das J.
Sasai H.
Shibasaki M.
J. Am. Chem. Soc.
1999,
121:
4168
9b Yoshikawa N.
Kumagai N.
Matsunaga S.
Moll G.
Ohshima T.
Suzuki T.
Shibasaki M.
J. Am. Chem. Soc.
2001,
123:
2466
9c Gnanadesikan V.
Horiuchi Y.
Ohshima T.
Shibasaki M.
J. Am. Chem. Soc.
2004,
126:
7782
10a Yamagiwa N.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2003,
125:
16178
10b Yamagiwa N.
Qin H.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2005,
127:
13419
11 Yamada K.-i.
Harwood SJ.
Gröger H.
Shibasaki M.
Angew. Chem. Int. Ed.
1999,
38:
3504
12 Trost BM.
Science (Washington, D.C.)
1991,
254:
1471
13a Palomo C.
Oiarbide M.
Laso A.
Eur. J. Org. Chem.
2007,
2561
13b Boruwa J.
Gogoi N.
Saikia PP.
Barua NC.
Tetrahedron: Asymmetry
2006,
17:
3315
13c Palomo C.
Oiarbide M.
Mielgo A.
Angew. Chem. Int. Ed.
2004,
43:
5442
14a Christensen C.
Juhl K.
Jørgensen KA.
Chem. Commun.
2001,
2222
14b Christensen C.
Juhl K.
Hazell RG.
Jørgensen KA.
J. Org. Chem.
2002,
67:
4875
14c Lu S.-F.
Du D.-M.
Zhang S.-W.
Xu J.
Tetrahedron: Asymmetry
2004,
15:
3433
14d Du D.-M.
Lu S.-F.
Fang T.
Xu J.
J. Org. Chem.
2005,
70:
3712
14e Choudary BM.
Ranganath KVS.
Pal U.
Kantam ML.
Sreedhar B.
J. Am. Chem. Soc.
2005,
127:
13167
14f Li H.
Wang B.
Deng L.
J. Am. Chem. Soc.
2006,
128:
732
14g Qin B.
Xiao X.
Liu X.
Huang J.
Wen Y.
Feng X.
J. Org. Chem.
2007,
72:
10302
14h Takada K.
Takemura N.
Cho K.
Sohtome Y.
Nagasawa K.
Tetrahedron Lett.
2008,
49:
1623
15a Misumi Y.
Bulman RA.
Matsumoto K.
Heterocycles
2002,
56:
599
15b Tur F.
Saá JM.
Org. Lett.
2007,
9:
5079
16 List B.
Shabat D.
Zhong G.
Turner JM.
Li A.
Bui T.
Anderson J.
Lerner RA.
Barbas CF.
J. Am. Chem. Soc.
1999,
121:
7283 ; and references cited therein
17a Vedejs E.
Jure M.
Angew. Chem. Int. Ed.
2005,
44:
3974
17b Angione MC.
Miller SJ.
Tetrahedron
2006,
62:
5254 ; and references cited therein
18a Ding K.
Du H.
Yuan Y.
Long J.
Chem. Eur. J.
2004,
10:
2872
18b de Vries JG.
Lefort L.
Chem. Eur. J.
2006,
12:
4722
18c Long J.
Hu J.
Shen X.
Ji B.
Ding K.
J. Am. Chem. Soc.
2002,
124:
10
18d Reetz MT.
Shell T.
Meiswinkel A.
Mehler G.
Angew. Chem. Int. Ed.
2003,
42:
790
18e Peña D.
Minnaard AJ.
Boogers JAF.
de Vries AHM.
de Vries JG.
Feringa BL.
Org. Biomol. Chem.
2003,
1:
1087
19 Tosaki S.-y.
Hara K.
Gnanadesikan V.
Morimoto H.
Harada S.
Sugita M.
Yamagiwa N.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2006,
128:
11776
20a Bari LD.
Lelli M.
Salvadori P.
Chem. Eur. J.
2004,
10:
4594
20b Yamagiwa N.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2004,
43:
4493
20c Horiuchi Y.
Gnanadesikan V.
Ohshima T.
Masu H.
Katagiri K.
Sei Y.
Yamaguchi K.
Shibasaki M.
Chem. Eur. J.
2005,
11:
5195
21 Lebel H.
Marcoux J.
Molinaro C.
Charette AB.
Chem. Rev.
2003,
103:
977
22 Corey EJ.
Chaykovsky M.
J. Am. Chem. Soc.
1965,
87:
1353
23a Aggarwal VK.
Alonso E.
Fang GY.
Ferrara M.
Hynd G.
Porcelloni M.
Angew. Chem. Int. Ed.
2001,
40:
1433 ; and references cited therein
23b Papageorgiou CD.
Cubillo de Dios MA.
Ley SV.
Gaunt MJ.
Angew. Chem. Int. Ed.
2004,
43:
4641
24a Kunz RK.
MacMillan DWC.
J. Am. Chem. Soc.
2005,
127:
3240
24b Hartikka A.
Arvidsson PI.
J. Org. Chem.
2007,
72:
5874
c Hartikka A.
Slósarczyka AT.
Arvidsson PI.
Tetrahedron: Asymmetry
2007,
18:
1403
2c , see:
25a Harada T.
Tuyet TMT.
Oku A.
Org. Lett.
2000,
2:
1319
25b Kakei H.
Tsuji R.
Ohshima T.
Morimoto H.
Matsunaga S.
Shibasaki M.
Chem. Asian J.
2007,
2:
257 ; and references cited therein
26 Kakei H.
Sone T.
Sohtome Y.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2007,
129:
13410
N -acylpyrroles as an ester surrogate, see:
27a Matsunaga S.
Kinoshita T.
Okada S.
Shibasaki M.
J. Am. Chem. Soc.
2004,
126:
7559
27b Matsunaga S.
Qin H.
Sugita M.
Okada S.
Kinoshita T.
Yamagiwa N.
Shibasaki M.
Tetrahedron
2006,
62:
6630 ; and references cited therein
28 Wooten AJ.
Carroll PJ.
Walsh PJ.
Org. Lett.
2007,
9:
3359
29 A related, dual control mechanism has been proposed by MacMillan, see reference 24a. See also, reference 10b for a related mechanism.
30 Coordination of a seventh ligand, such as H2 O, to the rare-earth-metal center was observed for rare-earth metals with a relatively large ionic radius, such as La, Pr, Eu; see references 8b, 8c, and 8e. Salvadori and co-workers reported different properties for Yb complexes; see reference 8d.
31a Brunel JM.
Holmes IP.
Angew. Chem. Int. Ed.
2004,
43:
2752
31b North M.
Tetrahedron: Asymmetry
2003,
14:
147
32a Yamagiwa N.
Tian J.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2005,
127:
3413
32b Tian J.
Yamagiwa N.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2002,
41:
3636
33a Tian S.-K.
Deng L.
J. Am. Chem. Soc.
2001,
123:
6195
33b Belokon’ YN.
Blacker AJ.
Clutterbuck LA.
North M.
Org. Lett.
2003,
5:
4505
33c Baeza A.
Casas J.
Nájera C.
Sansano JM.
Saá JM.
Angew. Chem. Int. Ed.
2003,
42:
3143
33d Lundgren S.
Wingstrand E.
Penhoat M.
Moberg C.
J. Am. Chem. Soc.
2005,
127:
11592 ; and references cited therein
34a Daikai K.
Kamaura M.
Inanaga J.
Tetrahedron Lett.
1998,
39:
7321
34b Nemoto T.
Ohshima T.
Yamaguchi K.
Shibasaki M.
J. Am. Chem. Soc.
2001,
123:
2725
34c Kinoshita T.
Okada S.
Park
S.-R.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2003,
42:
4680
34d Kino R.
Daikai K.
Kawanami T.
Furuno H.
Inanaga J.
Org. Biomol. Chem.
2004,
2:
1822
34e Chen Z.
Morimoto H.
Matsunaga S.
Shibasaki M.
Synlett
2006,
3529 ; see also reference 25b
35 Tian J.
Yamagiwa N.
Matsunaga S.
Shibasaki M.
Org. Lett.
2003,
5:
3021
36a Abiko Y.
Yamagiwa N.
Sugita M.
Tian J.
Matsunaga S.
Shibasaki M.
Synlett
2004,
2434
36b Yamagiwa N.
Abiko Y.
Sugita M.
Tian J.
Matsunaga S.
Shibasaki M.
Tetrahedron: Asymmetry
2006,
17:
566
37a Baeza A.
Casas J.
Nájera C.
Sansano JM.
Saá JM.
Angew. Chem. Int. Ed.
2003,
42:
3143
37b Baeza A.
Nájera C.
Sansano JM.
Saá JM.
Chem. Eur. J.
2005,
11:
3849
38a Hamashima Y.
Sawada D.
Kanai M.
Shibasaki M.
J. Am. Chem. Soc.
1999,
121:
2641
38b Ryu DH.
Corey EJ.
J. Am. Chem. Soc.
2004,
126:
8106
39 Morimoto H.
Lu G.
Aoyama N.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2007,
129:
9588
40a Marques MMB.
Angew. Chem. Int. Ed.
2006,
45:
348
40b Córdova A.
Acc. Chem. Res.
2004,
37:
102
40c Shibasaki M.
Matsunaga S.
J. Organomet. Chem.
2006,
691:
2089
40d Kobayashi S.
Ueno M. In Comprehensive Asymmetric Catalysis
Suppl. 1:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
2003.
Chap. 29.5.
p.143
40e Friestad GK.
Mathies AK.
Tetrahedron
2007,
63:
2541
41 3 in organic synthesis, see: Kobayashi S.
Sugiura M.
Kitagawa H.
Lam WW.-L.
Chem. Rev.
2002,
102:
2227
42a Desimoni G.
Faita G.
Quadrelli P.
Chem. Rev.
2003,
103:
3119
3 /pybox complex as a bifunctional catalyst to generate a nucleophilic RE-cyanide species, see:
42b Schaus SE.
Jacobsen EN.
Org. Lett.
2000,
2:
1001
42c Keith JM.
Jacobsen EN.
Org. Lett.
2004,
6:
153
43a Marigo M.
Kjærsgaard A.
Juhl K.
Gathergood N.
Jørgensen KA.
Chem. Eur. J.
2003,
9:
2359
43b Uraguchi D.
Terada M.
43c Hamashima Y.
Sasamoto N.
Hotta D.
Somei H.
Umebayashi N.
Sodeoka M.
Angew. Chem. Int. Ed.
2005,
44:
1525
43d Lou S.
Taoka BM.
Ting A.
Schaus SE.
J. Am. Chem. Soc.
2005,
127:
11256
43e Song J.
Wang Y.
Deng L.
J. Am. Chem. Soc.
2006,
128:
6048
43f Sasamoto N.
Dubs C.
Hamashima Y.
Sodeoka M.
J. Am. Chem. Soc.
2006,
128:
14010
43g Tillman AL.
Ye J.
Dixon DJ.
Chem. Commun.
2006,
1191 ; for other examples, see the reviews in reference 40
44a Saito S.
Tsubogo T.
Kobayashi S.
Chem. Commun.
2007,
1236
44b Kumagai N.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2004,
126:
13632
44c Ricci A.
Pettersen D.
Bernardi L.
Fini F.
Fochi M.
Herrera RP.
Sgarzani V.
Adv. Synth. Catal.
2007,
349:
1037
44d Yamaguchi A.
Aoyama N.
Matsunaga S.
Shibasaki M.
Org. Lett.
2007,
9:
3387
45 N -(2-hydroxyacetyl)pyrrole as an ester equivalent donor, see: Harada S.
Handa S.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2005,
44:
4365
46a Corey EJ.
Link JO.
46b Corey EJ.
Link JO.
Tetrahedron Lett.
1992,
33:
3431
46c Fujisawa T.
Ito T.
Fujimoto K.
Shimizu M.
Wynberg H.
Staring EGJ.
Tetrahedron Lett.
1997,
38:
1593
46d Wang Z.
Campagna S.
Yang K.
Xu G.
Pierce ME.
Fortunak JM.
Confalone PN.
J. Org. Chem.
2000,
65:
1889
46e Jiang B.
Si Y.-G.
Adv. Synth. Catal.
2004,
346:
669
46f Bejot R.
Tisserand S.
Reddy LM.
Barma DK.
Baati R.
Falck JR.
Mioskowski C.
Angew. Chem. Int. Ed.
2005,
44:
2008
47 17 as donors was first investigated in a racemic system; see: Morimoto H.
Wiedemann SH.
Yamaguchi A.
Harada S.
Chen Z.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2006,
45:
3146
48a Matsunaga S.
Kumagai N.
Harada S.
Shibasaki M.
J. Am. Chem. Soc.
2003,
125:
4712
48b Matsunaga S.
Yoshida T.
Morimoto H.
Kumagai N.
Shibasaki M.
48c Yoshida T.
Morimoto H.
Kumagai N.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2005,
44:
3470
48d Matsunaga S.
Sugita M.
Yamagiwa N.
Handa S.
Yamaguchi A.
Shibasaki M.
Bull. Chem. Soc. Jpn.
2006,
79:
1906
N -heteroarylsulfonyl imines in asymmetric synthesis, see:
49a González AS.
G ómez Arrayás R.
Carretero JC.
Org. Lett.
2006,
8:
2977 ; and references cited therein
49b Esquivias J.
Gómez Arrayás R.
Carretero JC.
J. Am. Chem. Soc.
2007,
129:
1480
49c Nakamura S.
Nakashima H.
Sugimoto H.
Shibata N.
Toru T.
Tetrahedron Lett.
2006,
47:
7599
49d Nakamura S.
Nakashima H.
Sugimoto H.
Sano H.
Hattori M.
Shibata N.
Toru T.
Chem. Eur. J.
2008,
14:
2145 ; and references cited therein
50 Trichloromethyl carbinols were stereoselectively converted into azetidinecarboxylic acids; see reference 47.
51 Handa S.
Gnanadesikan V.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2007,
129:
4900
52a Annamalai V.
DiMauro EF.
Carroll PJ.
Kozlowski MC.
J. Org. Chem.
2003,
68:
1973 ; and references cited therein See also:
52b Sammis GM.
Danjo H.
Jacobsen EN.
J. Am. Chem. Soc.
2004,
126:
9928
52c Li W.
Thakur SS.
Chen S.-W.
Shin C.-K.
Kawthekar RB.
Kim G.-J.
Tetrahedron Lett.
2006,
47:
3453 ; and references cited therein
53a Koner R.
Lee G.-H.
Wang Y.
Wei H.-H.
Mohanta S.
Eur. J. Inorg. Chem.
2005,
1500
53b Benelli C.
Guerriero P.
Tamburini S.
Vigato PA.
Mater. Chem. Phys.
1992,
31:
137 ; and references cited therein
54 Westermann B.
Angew. Chem. Int. Ed.
2003,
42:
151
anti -selective catalytic asymmetric nitro-Mannich reactions with metal catalysts, see:
55a Yamada K.-I.
Moll G.
Shibasaki M.
Synlett
2001,
980
55b Knudsen KR.
Risgaard T.
Nishiwaki N.
Gothelf KV.
Jørgensen KA.
J. Am. Chem. Soc.
2001,
123:
5843 ; and references cited therein
55c Anderson JC.
Howell GP.
Lawrence RM.
Wilson CS.
J. Org. Chem.
2005,
70:
5665
55d Yoon TP.
Jacobsen EN.
Angew. Chem. Int. Ed.
2005,
44:
466
55e Xu X.
Furukawa T.
Okino T.
Miyabe H.
Takemoto Y.
Chem. Eur. J.
2006,
12:
466
55f Robak MT.
Trincado M.
Ellman JA.
J. Am. Chem. Soc.
2007,
129:
15110
55g Nugent BM.
Yoder RA.
Johnston JN.
J. Am. Chem. Soc.
2004,
126:
3418
55h Palomo C.
Oiarbide M.
Laso A.
López R.
J. Am. Chem. Soc.
2005,
127:
17622
56a Kato N.
Mita T.
Kanai M.
Therrien B.
Kawano M.
Yamaguchi K.
Danjo H.
Sei Y.
Sato A.
Furusho S.
Shibasaki M.
56b Wooten AJ.
Salvi L.
Carroll PJ.
Walsh PJ.
Adv. Synth. Catal.
2007,
349:
561
syn -selective direct catalytic asymmetric nitroaldol reactions, see:
57a Sasai H.
Tokunaga T.
Watanabe S.
Suzuki T.
Itoh N.
Shibasaki M.
J. Org. Chem.
1995,
60:
7388
57b Sohtome Y.
Hashimoto Y.
Nagasawa K.
Eur. J. Org. Chem.
2006,
2894
57c Sohtome Y.
Takemura N.
Takada K.
Takagi R.
Iguchi T.
Nagasawa K.
Chem. Asian J.
2007,
2:
1150
57d Arai T.
Watanabe M.
Yanagisawa A.
Org. Lett.
2007,
9:
3595
anti -selective catalytic asymmetric nitroaldol reactions using silyl nitronates, see:
58a Ooi T.
Doda K.
Maruoka K.
J. Am. Chem. Soc.
2003,
125:
2054
58b Risgaard T.
Gothelf KV.
Jørgensen KA.
Org. Biomol. Chem.
2003,
1:
153
anti -selective direct catalytic asymmetric nitroaldol reactions, see:
59a Uraguchi D.
Sakaki S.
Ooi T.
J. Am. Chem. Soc.
2007,
129:
12392
59b Purkarthofer T.
Gruber K.
Gruber-Khadjawi M.
Waich K.
Skranc W.
Mink D.
Griengl H.
Angew. Chem. Int. Ed.
2006,
45:
3454
59c Nitabaru T.
Kumagai N.
Shibasaki M.
Tetrahedron Lett.
2008,
49:
272
60 Handa S.
Nagawa K.
Sohtome Y.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2008,
47:
3230
61 Yamazaki N, Fukuda Y, Shibazaki Y, Niizato T, Kosugi I, and Yoshioka S. inventors; US Patent 5,449,694.
; and references cited therein
62 Tanaka N, and Tamai T. inventors; JP Patent JP2002-64840.
; and references cited therein
63 Chen Z.
Morimoto H.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2008,
130:
2170
64a Knudsen KR.
Jørgensen KA.
Org. Biomol. Chem.
2005,
3:
1362
64b Singh A.
Yoder RA.
Shen B.
Johnston JN.
J. Am. Chem. Soc.
2007,
129:
3466
65 Viso A.
Fernández de la Pradilla R.
García A.
Flores A.
Chem. Rev.
2005,
105:
3167
66a Negoro T.
Murata M.
Ueda S.
Fujitani B.
Ono Y.
Kuromiya A.
Suzuki K.
Matsumoto J.-I.
J. Med. Chem.
1998,
41:
4118
66b Kurono M.
Fujiwara I.
Yoshida K.
Biochemistry
2001,
40:
8216
66c Bril V.
Buchanan RA.
Diabetes Care
2004,
27:
2369
66d Kurono M.
Fujii A.
Murata M.
Fujitani B.
Negoro T.
Biochem. Pharmacol.
2006,
71:
338
66e Giannoukakis N.
Curr. Opin. Invest. Drugs
2006,
7:
916
67a Diels O.
Justus Liebigs Ann. Chem.
1922,
429:
1
67b Diels O.
Behncke H.
Ber. Dtsch. Chem. Ges.
1924,
57:
653
68a Marigo M.
Juhl K.
Jørgensen KA.
Angew. Chem. Int. Ed.
2003,
42:
1367
68b Ma S.
Jiao N.
Zheng Z.
Ma Z.
Lu Z.
Ye L.
Deng Y.
Chen G.
Org. Lett.
2004,
6:
2193
68c Foltz C.
Stecker B.
Marconi G.
Bellemin-Laponnaz S.
Wadepohl H.
Gabe LH.
Chem. Commun.
2005,
5115
68d Kim YK.
Kim DY.
Tetrahedron Lett.
2006,
47:
4565
68e Comelles J.
Pericas .
Moreno-Mañas M.
Vallribera A.
Drudis-Solé G.
Lledos A.
Parella T.
Roglans A.
García-Granda S.
Roces-Fernández L.
J. Org. Chem.
2007,
72:
2077
69a Sabby S.
Bella M.
Jørgensen KA.
J. Am. Chem. Soc.
2004,
126:
8120
69b Pihko PM.
Pohjakallio A.
Synlett
2004,
2115
69c Liu X.
Li H.
Deng L.
Org. Lett.
2005,
7:
167
69d Xu X.
Yabuta T.
Yuan P.
Takemoto Y.
Synlett
2006,
137
69e Terada M.
Nakano M.
Ube H.
J. Am. Chem. Soc.
2006,
128:
16044
70a Mashiko T.
Hara K.
Tanaka D.
Fujiwara Y.
Kumagai N.
Shibasaki M.
J. Am. Chem. Soc.
2007,
129:
11342
70b Mashiko T., Kumagai N., Shibasaki M.; manuscript in preparation.
