Abstract
Our research group was the first to discover that cationic rhodium(I)/BINAP-type bisphosphine complexes are versatile new catalysts for highly chemo-, regio-, and enantioselective [2+2+2] cycloadditions. The high chemo- and regioselectivity of these cycloadditions enabled efficient catalytic synthesis of substituted benzenes, cyclophanes, and nitrogen heterocycles. Furthermore, enantioselective variants of these cycloadditions were also developed that realized efficient catalytic constructions of axial, planar, central, and spiro chirality.
1 Introduction
2 Chemo- and Regioselective [2+2+2] Cycloadditions
2.1 [2+2+2] Cycloaddition of Terminal Alkynes
2.2 [2+2+2] Cycloaddition of Two Different Alkynes
2.3 [2+2+2] Cycloaddition of α,ω-Diynes with Alkynes
2.4 [2+2+2] Cycloaddition of Alkynes with Isocyanates, Isothiocyanates, and Carbon Disulfide
2.5 [2+2+2] Cycloaddition of Alkynes with Nitriles
3 Enantioselective [2+2+2] Cycloadditions
3.1 Construction of Axial Chirality
3.2 Construction of Planar Chirality
3.3 Construction of Central Chirality
3.4 Construction of Spiro Chirality
4 Summary
Key words
alkynes - asymmetric catalysis - BINAP - cycloadditions - rhodium
References
1a Wender PA.
Croatt MP.
Deschamps NM. In Comprehensive Organometallic Chemistry
3rd ed., Vol. 10:
Mingos DMP.
Crabtree RH.
Ojima I.
Elsevier;
Oxford:
2007.
p.603
1b Yet L.
Chem. Rev.
2000,
100:
2963
1c Mehta G.
Singh V.
Chem. Rev.
1999,
99:
881
1d Ojima I.
Tzamarioudaki M.
Li Z.
Donovan RJ.
Chem. Rev.
1996,
96:
635
1e Lautens M.
Klute W.
Tam W.
Chem. Rev.
1996,
96:
49
1f Schore NE.
Chem. Rev.
1988,
88:
1081
2 Sato Y.
Nishimata T.
Mori M.
J. Org. Chem.
1994,
59:
6133
3 Stará IG.
Stary I.
Kollarovic A.
Teply F.
Vyskocil S.
Saman D.
Tetrahedron Lett.
1999,
40:
1993
4a Tanaka K.
Qiao S.
Tobisu M.
Lo MM.-C.
Fu GC.
J. Am. Chem. Soc.
2000,
122:
9870
4b Tanaka K.
Fu GC.
J. Org. Chem.
2001,
66:
8177
5a Tanaka K.
Fu GC.
J. Am. Chem. Soc.
2001,
123:
11492
5b Tanaka K.
Fu GC.
Angew. Chem. Int. Ed.
2002,
41:
1607
5c Tanaka K.
Fu GC.
Chem. Commun.
2002,
684
5d Tanaka K.
Fu GC.
Org. Lett.
2002,
4:
933
5e Tanaka K.
Fu GC.
J. Am. Chem. Soc.
2002,
124:
10296
5f Tanaka K.
Fu GC.
J. Am. Chem. Soc.
2003,
125:
8078
6 Reppe W.
Schweckendick WJ.
Justus Liebigs Ann. Chem.
1948,
560:
104
7a Chopade PR.
Louie J.
Adv. Synth. Catal.
2006,
348:
2307
7b Gandon V.
Aubert C.
Malacria M.
Chem. Commun. (Cambridge)
2006,
2209
7c Kotha S.
Brahmachary E.
Lahiri K.
Eur. J. Org. Chem.
2005,
4741
7d Yamamoto Y.
Curr. Org. Chem.
2005,
9:
503
7e Malacria M.
Aubert C.
Renaud JL. In Science of Synthesis : Houben-Weyl, Methods of Molecular Transformations
Vol. 1:
Lautens M.
Trost BM.
Thieme;
Stuttgart:
2001.
p.439
7f Saito S.
Yamamoto Y.
Chem. Rev.
2000,
100:
2901
7g Grotjahn DB. In Comprehensive Organometallic Chemistry II
Vol. 12:
Abel EW.
Stone FGA.
Wilkinson G.
Hegedus L.
Pergamon;
Oxford:
1995.
p.741
7h Boese R.
Sickle APV.
Vollhardt KPC.
Synthesis
1994,
1374
7i Schore NE.
In Comprehensive Organic Synthesis
Vol. 5:
Trost BM.
Fleming I.
Pergamon;
Oxford:
1991.
p.1129
7j Vollhardt KPC.
Angew. Chem., Int. Ed. Engl.
1984,
23:
539
8a Ozerov OV.
Ladipo FT.
Patrick BO.
J. Am. Chem. Soc.
1999,
121:
7941
8b Ozerov OV.
Patrick BO.
Ladipo FT.
J. Am. Chem. Soc.
2000,
122:
6423
8c Saito S.
Kawasaki T.
Tsuboya N.
Yamamoto Y.
J. Org. Chem.
2001,
66:
796
9a Vollhardt KPC.
Bergman RG.
J. Am. Chem. Soc.
1974,
96:
4996
9b Hillard RL.
Vollhardt KPC.
Angew. Chem., Int. Ed. Engl.
1975,
14:
712
9c Hillard RL.
Vollhardt KPC.
J. Am. Chem. Soc.
1977,
99:
4058
9d Vollhardt KPC.
Acc. Chem. Res.
1977,
10:
1
10 Fujiwara M.
Ojima I. In Modern Rhodium-Catalyzed Organic Reactions
Evans PA.
Wiley-VCH;
Weinheim:
2005.
Chap. 7.
p.129
11a Müller E.
Synthesis
1974,
761
11b Grigg R.
Scott R.
Stevenson P.
Tetrahedron Lett.
1982,
23:
2691
11c Grigg R.
Scott R.
Stevenson P.
J. Chem. Soc., Perkin Trans. 1
1988,
1357
11d Magnus P.
Witty D.
Stamford A.
Tetrahedron Lett.
1993,
34:
23
11e McDonald FE.
Zhu HYH.
Holmquist CR.
J. Am. Chem. Soc.
1995,
117:
6605
11f Kotha S.
Brahmachary E.
Tetrahedron Lett.
1997,
38:
3561
11g Grigg R.
Sridharan V.
Wang J.
Xu J.
Tetrahedron
2000,
56:
8967
11h Witulski B.
Stengel T.
Angew. Chem. Int. Ed.
1999,
38:
2426
11i Witulski B.
Alayrac C.
Angew. Chem. Int. Ed.
2002,
41:
3281
11j Witulski B.
Zimmermann A.
Gowans ND.
Chem. Commun.
2002,
2984
11k Witulski B.
Zimmermann A.
Synlett
2002,
1855
11l McDonald FE.
Smolentsev V.
Org. Lett.
2002,
4:
745
11m Nishiyama H.
Niwa E.
Inoue T.
Ishima Y.
Aoki K.
Organometallics
2002,
21:
2572
11n Kinoshita H.
Shinokubo H.
Oshima K.
J. Am. Chem. Soc.
2003,
125:
7784
11o Torrent A.
González I.
Pla-Quintana A.
Roglans A.
J. Org. Chem.
2005,
70:
2033
11p Novak P.
Pohl R.
Kotora M.
Hocek M.
Org. Lett.
2006,
8:
2051
11q Tracey MR.
Oppenheimer J.
Hsung RP.
J. Org. Chem.
2006,
71:
8629
12a Ohshita J.
Furumori K.
Matsuguchi A.
Ishikawa M.
J. Org. Chem.
1990,
55:
3277
12b Field LD.
Ward AJ.
Turner P.
Aust. J. Chem.
1999,
52:
1085
13 Robinson JE. In Modern Rhodium-Catalyzed Organic Reactions
Evans PA.
Wiley-VCH;
Weinheim:
2005.
p.241
14a Baidossi W.
Goren N.
Blum J.
J. Mol. Catal.
1993,
85:
153
14b Doyle MP.
Shanklin MS.
Organometallics
1994,
13:
1081
14c Yan H.
Beatty AM.
Fehlner TP.
Organometallics
2002,
21:
5029
15 Tanaka K.
Shirasaka K.
Org. Lett.
2003,
5:
4697
16 Tanaka K.
Toyoda K.
Wada A.
Shirasaka K.
Hirano M.
Chem. Eur. J.
2005,
11:
1145
17 Saito T.
Yokozawa T.
Ishizaki T.
Moroi T.
Sayo N.
Miura T.
Kumobayashi H.
Adv. Synth. Catal.
2001,
343:
264
18 Zhang X.
Mashima K.
Koyano K.
Sayo N.
Kumobayashi H.
Akutagawa S.
Takaya H.
Tetrahedron Lett.
1991,
32:
7283
19a Ura Y.
Sato Y.
Tsujita H.
Kondo T.
Imachi M.
Mitsudo T.
J. Mol. Catal. A: Chem.
2005,
239:
166
19b Ura Y.
Sato Y.
Shiotsuki M.
Kondo T.
Mitsudo T.
J. Mol. Catal. A: Chem.
2004,
209:
35
19c Takeuchi R.
Nakaya Y.
Org. Lett.
2003,
5:
3659
19d Mori N.
Ikeda S.-I.
Odashima K.
Chem. Commun.
2001,
181
19e Dieck TH.
Munz C.
Müller C.
J. Organomet. Chem.
1990,
384:
243
19f Abdulla K.
Booth BL.
Stacey C.
J. Organomet. Chem.
1985,
293:
103
20 Tanaka K.
Nishida G.
Ogino M.
Hirano M.
Noguchi K.
Org. Lett.
2005,
7:
3119
21a Boñaga LVR.
Zhang H.-C.
Moretto AF.
Ye H.
Gautheir DA.
Li J.
Leo GC.
Maryanoff BE.
J. Am. Chem. Soc.
2005,
127:
3473
21b Boñaga LVR.
Zhang H.-C.
Maryanoff BE.
Chem. Commun.
2004,
2394
21c Boñaga LVR.
Zhang H.-C.
Gautheir DA.
Reddy I.
Maryanoff BE.
Org. Lett.
2003,
5:
4537
21d Moretto AF.
Zhang H.-C.
Maryanoff BE.
J. Am. Chem. Soc.
2001,
123:
3157
22 Tanaka K.
Sagae H.
Toyoda K.
Noguchi K.
Eur. J. Org. Chem.
2006,
3575
23a Nakamura I.
Yamamoto Y.
Chem. Rev.
2004,
104:
2127
23b Varela JA.
Saá C.
Chem. Rev.
2003,
103:
3787
24a Hong P.
Yamazaki H.
Synthesis
1977,
50
24b Hong P.
Yamazaki H.
Tetrahedron Lett.
1977,
1333
24c Earl RA.
Vollhardt KPC.
J. Org. Chem.
1984,
49:
4786
24d Diversi P.
Ingrosso G.
Lucherini A.
Malquori S.
J. Mol. Catal.
1987,
40:
267
24e Hoberg H.
Oster BW.
Synthesis
1982,
324
24f Hoberg H.
Oster BW.
J. Organomet. Chem.
1982,
234:
C35
24g Hoberg H.
Oster BW.
J. Organomet. Chem.
1983,
252:
359
24h Duong HA.
Cross MJ.
Louie J.
J. Am. Chem. Soc.
2004,
126:
11438
24i Duong HA.
Louie J.
Tetrahedron
2006,
62:
7552
24j Yamamoto Y.
Takagishi H.
Itoh K.
Org. Lett.
2001,
3:
2117
24k Yamamoto Y.
Kinpara K.
Saigoku T.
Takagishi H.
Okuda S.
Nishiyama H.
Itoh K.
J. Am. Chem. Soc.
2005,
127:
605
25a Flynn ST.
Hasso-Henderson SE.
Parkins AW.
J. Mol. Catal.
1985,
32:
101
25b Yu RT.
Rovis T.
J. Am. Chem. Soc.
2006,
128:
2782
25c Yu RT.
Rovis T.
J. Am. Chem. Soc.
2006,
128:
12370
25d Kondo T.
Nomura M.
Ura Y.
Wada K.
Mitsudo T.
Tetrahedron Lett.
2006,
47:
7107
26 Tanaka K.
Wada A.
Noguchi K.
Org. Lett.
2005,
7:
4737
27 Tanaka K.
Wada A.
Noguchi K.
Org. Lett.
2006,
8:
907
28a Wakatsuki Y.
Yamazaki H.
J. Chem. Soc., Chem. Commun.
1973,
280
28b Yamamoto Y.
Takagishi H.
Itoh K.
J. Am. Chem. Soc.
2002,
124:
28
29 Beesley RM.
Ingold CK.
Thorpe JF.
J. Chem. Soc.
1915,
1080
30a Wakatsuki Y.
Yamazaki H.
J. Chem. Soc., Dalton Trans.
1978,
1278
30b Bönnemann H.
Brinkmann R.
Synthesis
1975,
600
30c Bönnemann H.
Angew. Chem., Int. Ed. Engl.
1978,
17:
505
30d See also reference 28a.
31a Naiman A.
Vollhardt KPC.
Angew. Chem., Int. Ed. Engl.
1977,
16:
708
31b Brien DJ.
Naiman A.
Vollhardt KPC.
J. Chem. Soc., Chem. Commun.
1982,
133
31c Parnell CA.
Vollhardt KPC.
Tetrahedron
1985,
41:
5791
32a Fatland AW.
Eaton BE.
Org. Lett.
2000,
2:
3131
32b Heller B.
Sundermann B.
Buschmann H.
Drexler H.-J.
You J.
Holzgrabe U.
Heller E.
Oehme G.
J. Org. Chem.
2002,
67:
4414
32c Gutnov A.
Abaev V.
Redkin D.
Fischer C.
Bonrath W.
Heller B.
Synlett
2005,
1188
32d Groth U.
Huhn T.
Kesenheimer C.
Kalogerakis A.
Synlett
2005,
1758
32e Hrdina R.
Stará I.
Dufková L.
Mitchel S.
Cisarová I.
Kotora M.
Tetrahedron
2006,
62:
968
32f Zhou Y.
Porco JA.
Snyder JK.
Org. Lett.
2007,
9:
393
32g Chang H.-T.
Jeganmohan M.
Cheng C.-H.
Org. Lett.
2007,
9:
505
32h Kase K.
Goswami A.
Ohtaki K.
Tanabe E.
Saino N.
Okamoto S.
Org. Lett.
2007,
9:
931
32i Yamamoto Y.
Okuda S.
Itoh K.
Chem. Commun.
2001,
1102
32j Yamamoto Y.
Ogawa R.
Itoh K.
J. Am. Chem. Soc.
2001,
123:
6189
32k Varela JA.
Castedo L.
Saà C.
J. Org. Chem.
2003,
68:
8595
32l Yamamoto Y.
Kinpara K.
Nishiyama H.
Itoh K.
Adv. Synth. Catal.
2005,
347:
1913
32m Yamamoto Y.
Kinpara K.
Ogawa R.
Nishiyama H.
Itoh K.
Chem. Eur. J.
2006,
12:
5618
32n McCormick MM.
Duong HA.
Zuo G.
Louie J.
J. Am. Chem. Soc.
2005,
127:
5030
32o Takevec TN.
Zuo G.
Simon K.
Louie J.
J. Org. Chem.
2006,
71:
5834
33a Cioni P.
Diversi P.
Ingrosso G.
Lucherini A.
Ronca P.
J. Mol. Catal.
1987,
40:
337
33b Cioni P.
Diversi P.
Ingrosso G.
Lucherini A.
Ronca P.
J. Mol. Catal.
1987,
40:
359
34 Tanaka K.
Suzuki N.
Nishida G.
Eur. J. Org. Chem.
2006,
3917
35 Grigg R.
Scott R.
Stevenson P.
J. Chem. Soc., Perkin Trans. 1
1988,
1365
36a Bringmann G.
Mortimer AJP.
Keller PA.
Gresser MJ.
Garner J.
Breuning M.
Angew. Chem. Int. Ed.
2005,
44:
5384
36b Bringmann G.
Günther C.
Ochse M.
Schupp O.
Tasler S. In Progress in the Chemistry of Organic Natural Products
Vol. 82:
Herz W.
Falk H.
Kirby GW.
Moore RE.
Springer;
Vienna:
2001.
p.1
3 central chirality to axial chirality, see:
37a Nishii Y.
Wakasugi K.
Koga K.
Tanabe Y.
J. Am. Chem. Soc.
2004,
126:
5358
37b Bao J.
Wulff WD.
Fumo MJ.
Grant EB.
Heller DP.
Whitcomb MC.
Yeung S.-M.
J. Am. Chem. Soc.
1996,
118:
2166
38 Sato Y.
Ohashi K.
Mori M.
Tetrahedron Lett.
1999,
40:
5231
39 Tanaka K.
Nishida G.
Wada A.
Noguchi K.
Angew. Chem. Int. Ed.
2004,
43:
6510
40 Gutnov A.
Heller B.
Fischer C.
Drexler H.-J.
Spannenberg A.
Sundermann B.
Sundermann C.
Angew. Chem. Int. Ed.
2004,
43:
3795
41 Shibata T.
Fujimoto T.
Yokota K.
Takagi K.
J. Am. Chem. Soc.
2004,
126:
8382
42a Shimizu H.
Nagasaki I.
Saito T.
Tetrahedron
2005,
61:
5405
42b Hayashi T.
Acc. Chem. Res.
2000,
33:
354
43 Wallace TW.
Org. Biomol. Chem.
2006,
4:
3197
44 Yin J.
Buchwald SL.
J. Am. Chem. Soc.
2000,
122:
12051
45 Nishida G.
Suzuki N.
Noguchi K.
Tanaka K.
Org. Lett.
2006,
8:
3489
46a Yamamoto Y.
Hata K.
Arakawa T.
Itoh K.
Chem. Commun.
2003,
1290
46b Yamamoto Y.
Saigoku T.
Ohgai T.
Nishiyama H.
Itoh K.
Chem. Commun.
2004,
2702
46c Yamamoto Y.
Saigoku T.
Nishiyama H.
Ohgai T.
Itoh K.
Org. Biomol. Chem.
2005,
3:
1768
46d See also references 9c and 11e.
47 Tanaka K.
Suda T.
Noguchi K.
Hirano M.
J. Org. Chem.
2007,
72:
2243
48a Kitagawa O.
Yoshikawa M.
Tanabe H.
Morita T.
Takahashi M.
Dobashi Y.
Taguchi T.
J. Am. Chem. Soc.
2006,
128:
12923
48b Kitagawa O.
Takahashi M.
Yoshikawa M.
Taguchi T.
J. Am. Chem. Soc.
2005,
127:
3676
48c Kitagawa O.
Kohriyama M.
Taguchi T.
J. Org. Chem.
2002,
67:
8682
48d Terauchi J.
Curran DP.
Tetrahedron: Asymmetry
2003,
14:
587
49 For RhCl(PPh3 )3 -catalyzed [2+2+2] cycloadditions involving alkynamides, see refs 11h, 11i, and 11q.
50 Tanaka K.
Takeishi K.
Noguchi K.
J. Am. Chem. Soc.
2006,
128:
4586
51 Ashburn BO.
Carter RG.
Angew. Chem. Int. Ed.
2006,
45:
6737
52 Heller B.
Gutnov A.
Fischer C.
Drexler H.-J.
Spannenberg A.
Redkin D.
Sundermann C.
Sundermann B.
Chem. Eur. J.
2007,
13:
1117
53 Nishida G.
Noguchi K.
Hirano M.
Tanaka K.
Angew. Chem. Int. Ed.
2007,
46:
3951
54 ortho to the phosphorus center of achiral biaryl monophosphines may lock the ligand into a certain conformation, which plays an important role in the palladium-catalyzed cross-coupling reactions, see: Burgos CH.
Barder TE.
Huang X.
Buchwald SL.
Angew. Chem. Int. Ed.
2006,
45:
4321
55a Modern Cyclophane Chemistry
Gleither R.
Hopf H.
Wiley;
Chichester:
2004.
55b Cyclophane Chemistry
Vögtle F.
Wiley;
Chichester:
1993.
56 Kane VV.
De Wolff WH.
Bickelhaupt F.
Tetrahedron
1994,
50:
4574
57 Wijsman GW.
de Kanter FJJ.
de Wolf WH.
Bickelhaupt F.
Eur. J. Org. Chem.
2001,
2743
58 Tanaka K.
Sagae H.
Toyoda K.
Noguchi K.
Hirano M.
J. Am. Chem. Soc.
2007,
129:
1522
59 For rhodium-catalyzed macrocyclizations to form ortho- and metacyclophanes via intramolecular [2+2+2] cycloaddition of triynes in an aqueous-organic biphasic system, see reference 11n.
n ]metacyclophanes, see:
60a Piatek P.
Kalisiak J.
Jurczak J.
Tetrahedron Lett.
2004,
45:
3309
60b Kubik S.
Goddard R.
J. Org. Chem.
1999,
64:
9475
60c Grimme S.
Harren J.
Sobanski A.
Vögtle F.
Eur. J. Org. Chem.
1998,
1491
61 Pugin B, Martin P, Mueller M, Naud F, Spindler F, Thommen M, Melone G, and Kesselgruber M. inventors; WO 2004089920.
62 For examples of transesterification in metal-catalyzed [2+2+2] cycloadditions, see references 19c, 19e, and 19f.
63a Yamamoto Y.
Ishi J.
Nishiyama H.
Itoh K.
J. Am. Chem. Soc.
2004,
126:
3712
63b Yamamoto Y.
Ishi J.
Nishiyama H.
Itoh K.
J. Am. Chem. Soc.
2005,
127:
9625
64 Tanaka K.
Osaka T.
Noguchi K.
Hirano M.
Org. Lett.
2007,
9:
1307
65 For the synthesis of chiral phthalides by RhCl(PPh3 )3 -catalyzed [2+2+2] cycloadditions of ester-linked diynes with acetylene, see references 11k and 11l.
66a Chan ASC.
Hu W.
Pai C.-C.
Lau C.-P.
Jiang Y.
Mi A.
Yan M.
Sun J.
Lou R.
Deng J.
J. Am. Chem. Soc.
1997,
119:
9570
66b Arai MA.
Arai T.
Sasai H.
Org. Lett.
1999,
1:
1795
66c Hu A.-G.
Fu Y.
Xie J.-H.
Zhou H.
Wang L.-X.
Zhou Q.-L.
Angew. Chem. Int. Ed.
2002,
41:
2348
66d Xie J.-H.
Wang L.-X.
Fu Y.
Zhu S.-F.
Fan B.-M.
Duan H.-F.
Zhou Q.-L.
J. Am. Chem. Soc.
2003,
125:
4404
67a Takahashi T.
Tsutsui H.
Tamura M.
Kitagaki S.
Nakajima M.
Hashimoto S.
Chem. Commun.
2001,
1604
67b Tanaka M.
Takahashi M.
Sakamoto E.
Imai M.
Matsui A.
Fujio M.
Sakai K.
Suemune H.
Tetrahedron
2001,
57:
1197
68 Tsuchikama K.
Kuwata Y.
Shibata T.
J. Am. Chem. Soc.
2006,
128:
13686
69 Varela JA.
Castedo L.
Saá C.
Org. Lett.
1999,
1:
2141
70 Wada A.
Noguchi K.
Hirano M.
Tanaka K.
Org. Lett.
2007,
9:
1295
71 Burkinshaw SM.
Griffiths J.
Towns AD.
J. Mater. Chem.
1998,
8:
2677
72a Tanaka K.
Hara H.
Nishida G.
Hirano M.
Org. Lett.
2007,
9:
1907
72b Tanaka K.
Otake Y.
Wada A.
Hirano M.
Org. Lett.
2007,
9:
2203
72c Tanaka K.
Nishida G.
Sagae H.
Hirano M.
Synlett
2007,
1426
