RSS-Feed abonnieren
DOI: 10.1055/s-2005-869831
Power of Cooperativity: Lewis Acid-Lewis Base Bifunctional Asymmetric Catalysis
Publikationsverlauf
Publikationsdatum:
04. Mai 2005 (online)
![](https://www.thieme-connect.de/media/synlett/200510/lookinside/thumbnails/10.1055-s-2005-869831-1.jpg)
Abstract
The concept of bifunctional asymmetric catalysis is very powerful for designing new enantioselective catalysts. We describe our investigation starting with the development of a BINOL-derived Lewis acid-Lewis base bifunctional asymmetric catalyst for cyanosilylation of aldehydes. The initial establishment of the concept was followed by the development of new sugar-derived catalysts that promote general catalytic enantioselective cyanosilylation of ketones. We also describe the catalytic enantioselective Reissert reaction of pyridine derivatives and Strecker reaction of ketoimines as recent advances in this field.
1 Introduction
2 General Concept of Lewis Acid-Lewis Base Bifunctional Asymmetric Catalysis
3 Catalytic Enantioselective Cyanosilylation of Aldehydes and Aldimines
4 Catalytic Enantioselective Reissert Reaction of Quinolines and Isoquinolines
5 Catalytic Enantioselective Reissert Reaction of Pyridine Derivatives
6 Tetrasubstituted Carbon Construction as a Challenge in Asymmetric Catalysis
7 Catalytic Enantioselective Cyanosilylation of Ketones
8 Catalytic Enantioselective Strecker Reaction of Ketoimines
9 Summary
Key words
asymmetric synthesis - catalysis - Lewis acids - imines - pyridines
-
1a
Ma J.-A.Cahard D. Angew. Chem. Int. Ed. 2004, 43: 4566 -
1b
Shibasaki M.Kanai M.Funabashi K. Chem. Commun. 2002, 1989 -
1c
Shibasaki M.Kanai M. Chem. Pharm. Bull. 2001, 49: 511 -
1d
Rawlands GJ. Tetrahedron 2001, 57: 1865 -
1e
Shibasaki M.Sasai H.Arai T. Angew. Chem., Int. Ed. Engl. 1997, 36: 1236 - 2 Review:
Machajewski TD.Wong C.-H. Angew. Chem. Int. Ed. 2000, 39: 1352 -
3a
Evans DA.Truesdale LK.Carroll GL. J. Chem. Soc., Chem. Commun. 1973, 55 -
3b
Lidy W.Sundermeyer W. Chem. Ber. 1973, 106: 587 -
4a
Evans DA.Wong RY. J. Org. Chem. 1977, 42: 350 -
4b
Kobayashi S.Tsuchiya Y.Mukaiyama T. Chem. Lett. 1991, 537 - 5 For a recent review, see:
Brunel J.-M.Holmes IP. Angew. Chem. Int. Ed. 2004, 43: 2752 - For examples of bifunctional catalysts in enantioselective cyanosilylation of aldehydes, see:
-
6a
Kobayashi S.Tsuchiya Y.Mukaiyama T. Chem. Lett. 1991, 541 -
6b
Casas J.Nájera C.Sansano JM.Saá JM. Org. Lett. 2002, 4: 2589 -
6c
Rowlands GJ. Synlett 2003, 236 -
6d
Ryu DH.Corey EJ. J. Am. Chem. Soc. 2004, 126: 8106 - 7
Corey EJ.Helal CJ. Angew. Chem. Int. Ed. 1998, 37: 1986 - 8
Noyori R.Kitamura M. Angew. Chem., Int. Ed. Engl. 1991, 30: 49 -
9a
Hamashima Y.Sawada D.Kanai M.Shibasaki M. J. Am. Chem. Soc. 1999, 121: 2641 -
9b
Hamashima Y.Sawada D.Nogami H.Kanai M.Shibasaki M. Tetrahedron 2001, 57: 805 - For other examples of beneficial effects of a proton source in catalytic enantioselective reactions, see:
-
10a
Evans DA.Rovis T.Kozlowski MC.Tedow JS. J. Am. Chem. Soc. 1999, 121: 1994 -
10b
Josephsohn NS.Kuntz KW.Snapper ML.Hoveyda AH. J. Am. Chem. Soc. 2001, 123: 11594 -
10c
Yamashita Y.Ishitani H.Shimizu H.Kobayashi S. J. Am. Chem. Soc. 2002, 124: 3292 ; see also ref. 14 -
11a
Takamura M.Yanagisawa H.Kanai M.Shibasaki M. Chem. Pharm. Bull. 2002, 50: 1118 -
11b
Nogami H.Kanai M.Shibasaki M. Chem. Pharm. Bull. 2003, 51: 702 - 12
Sawada D.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2000, 122: 10521 - 13 For the observation of the isomerization of silyl nitriles to silyl isonitriles by IR, see:
Seckar JA.Thayer JS. Inorg. Chem. 1976, 15: 501 -
14a
Takamura M.Hamashima Y.Usuda H.Kanai M.Shibasaki M. Angew. Chem. Int. Ed. 2000, 39: 1650 -
14b
Takamura M.Hamashima Y.Usuda H.Kanai M.Shibasaki M. Chem. Pharm. Bull. 2000, 48: 1586 - 15
Nogami H.Matsunaga S.Kanai M.Shibasaki M. Tetrahedron Lett. 2001, 42: 279 - For reviews, see:
-
16a
Popp FD. Heterocycles 1973, 1: 165 -
16b
McEwen WE.Cobb RL. Chem. Rev. 1955, 55: 511 -
17a
Takamura M.Funabashi K.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2000, 122: 6327 -
17b
Takamura M.Funabashi K.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2001, 123: 6801 - 18
Leeson PD.Carling RW.Moore KW.Moseley AM.Smith JD.Stevenson G.Chan T.Baker R.Foster AC.Grimwood S.Kemp JA.Marshall GR.Hoogsteen K. J. Med. Chem. 1992, 35: 1954 - 19
Funabashi K.Ratni H.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2001, 123: 10784 - For recent reviews, see:
-
20a
Buffat MGP. Tetrahedron 2004, 60: 1701 -
20b
Laschat S.Dickner T. Synthesis 2000, 1781 - For selected examples, see:
-
21a
Comins DL.Goehring RR.Joseph SP.O’Connor S. J. Org. Chem. 1990, 55: 2574 -
21b
Gosmini R.Mangeney P.Alexakis A.Commerçon M.Normant J.-F. Synlett 1991, 111 -
21c
Génisson Y.Marazano C.Das BC. J. Org. Chem. 1993, 58: 2052 -
21d
Charette AB.Grenon M.Lemire A.Pourashraf M.Martel J. J. Am. Chem. Soc. 2001, 123: 11829 -
21e
Yamada S.Morita C. J. Am. Chem. Soc. 2002, 124: 8184 -
21f
Legault C.Charette AB. J. Am. Chem. Soc. 2003, 125: 6360 - 22
Reuss RH.Smith NG.Winters LJ. J. Org. Chem. 1974, 39: 2027 - 23
Popp FD.Takeuchi I.Kant J.Hamada Y. J. Chem. Soc., Chem. Commun. 1987, 1765 - 24
Ichikawa E.Suzuki M.Yabu K.Albert M.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2004, 126: 11808 - 25
Sanner MA.Chappie TA.Dunaiskis AR.Fliri AF.Desai KA.Zorn SH.Jackson ER.Johnson CG.Morrone JM.Seymour PA.Majchrzak MJ.Faraci WS.Collins JL.Duignan DB.Di Prete CC.Lee JS.Trozzi A. Bioorg. Med. Chem. Lett. 1998, 8: 725 - For recent examples of advances in this field, see:
-
26a
Dosa PI.Fu GC. J. Am. Chem. Soc. 1998, 120: 445 -
26b
Denmark SE.Fan Y. J. Am. Chem. Soc. 2002, 124: 4233 -
26c
Jeon S.-J.Walsh PJ. J. Am. Chem. Soc. 2003, 125: 9544 -
26d
Ramon DJ.Yus M. Tetrahedron Lett. 1998, 54: 5651 -
26e
Yamasaki S.Fujii K.Wada R.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2002, 124: 6536 -
26f
Wada R.Oisaki K.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2004, 126: 8910 -
26g
Suto Y.Kumagai N.Matsunaga S.Kanai M.Shibasaki M. Org. Lett. 2003, 5: 3147 -
26h
Oisaki K.Suto Y.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2003, 125: 5644 - 27 For example, see:
Kiljunen E.Kanerva LT. Tetrahedron: Asymmetry 1997, 8: 1151 - 28
Kanai M.Hamashima Y.Shibasaki M. Tetrahedron Lett. 2000, 41: 2405 - 29
Hamashima Y.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2000, 122: 7412 - For examples of catalytic enantioselective cyanation of ketones from other groups, see:
-
30a
Belokon’ YN.Green B.Ikonnikov NS.North M.Tararov VI. Tetrahedron Lett. 1999, 38: 6669 -
30b
Belokon’ YN.Caveda-Cepas S.Green B.Ikonnikov NS.Khrustalev VN.Larichev VS.Moscalenko MA.North M.Orizu C.Tararov VI.Tasinazzo M.Timofeeva GI.Yashkina LV. J. Am. Chem. Soc. 1999, 121: 3968 -
30c
Belokon’ YN.Green B.Ikonnikov NS.Larichev VS.Lokshin BV.Moscalenko MA.North M.Orizu C.Peregudov AS.Timofeeva GI. Eur. J. Org. Chem. 2000, 2655 -
30d
Belokon’ YN.Green B.Ikonnikov NS.North M.Parsons T.Tararov VI. Tetrahedron 2001, 57: 771 -
30e
Tian S.-K.Deng L. J. Am. Chem. Soc. 2001, 123: 6195 -
30f
Tian S.-K.Deng L. J. Am. Chem. Soc. 2003, 125: 9900 -
30g
Deng H.Isler MP.Snapper ML.Hoveyda AH. Angew. Chem. Int. Ed. 2002, 41: 1009 -
30h
Chen F.Feng Z.Qin B.Zhang G.Jiang Y. Org. Lett. 2003, 5: 949 -
30i
Shen Y.Feng X.Li Y.Zhang G.Jiang Y. Eur. J. Org. Chem. 2004, 129 - 31
Yabu K.Masumoto S.Yamasaki S.Hamashima Y.Kanai M.Du W.Curran DP.Shibasaki M. J. Am. Chem. Soc. 2001, 123: 9908 - 32
Fujii K.Maki K.Kanai M.Shibasaki M. Org. Lett. 2003, 5: 733 - 33
Takamura M.Yabu K.Nishi T.Yanagisawa H.Kanai M.Shibasaki M. Synlett 2003, 353 -
34a
Yabu K.Masumoto S.Kanai M.Curran DP.Shibasaki M. Tetrahedron Lett. 2002, 43: 2923 -
34b
Yabu K.Masumoto S.Kanai M.Shibasaki M. Heterocycles 2003, 59: 369 -
35a
Masumoto S.Suzuki M.Kanai M.Shibasaki M. Tetrahedron Lett. 2002, 43: 8647 -
35b
Masumoto S.Suzuki M.Kanai M.Shibasaki M. Tetrahedron 2004, 60: 10497 - For reviews, see:
-
36a
Cativiela C.Diaz-de-Villegas MD. Tetrahedron: Asymmetry 1998, 9: 3517 -
36b
Ohfune Y.Shinada T. Bull. Chem. Soc. Jpn. 2003, 76: 1115 -
37a
Gröger H. Chem. Rev. 2003, 103: 2795 -
37b
Spino C. Angew. Chem. Int. Ed. 2004, 43: 1764 -
38a
Vachal P.Jacobsen EN. Org. Lett. 2000, 2: 867 -
38b
Vachal P.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 10012 - 39
Chavarot M.Byrne JJ.Chavant PY.Vallée Y. Tetrahedron: Asymmetry 2001, 12: 1147 - 40
Masumoto S.Usuda H.Suzuki M.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2003, 125: 5634 - 41
Kato N.Suzuki M.Kanai M.Shibasaki M. Tetrahedron Lett. 2004, 45: 3147 - 42
Kato N.Suzuki M.Kanai M.Shibasaki M. Tetrahedron Lett. 2004, 45: 3153 - 43
Trost BM.Brown BS.McEachern EJ.Kuhn O. Chem.-Eur. J. 2003, 9: 4442 - 44
Trnka TM.Grubbs RH. Acc. Chem. Res. 2001, 34: 18 - 45
Kato N.Tomita D.Maki K.Kanai M.Shibasaki M. J. Org. Chem. 2004, 69: 6128 - 47 Recently, Jacobsen reported a catalytic enantioselective acyl-Pictet-Spengler reaction:
Taylor MS.Jacobsen EN. J. Am. Chem. Soc. 2004, 126: 10558
References
Chiral ligands are commercially available from Junsei Chemical Co., Ltd. [fax: +81 (3)32705461].
Note Added in Proof: During the review process for this Account, Corey et al. reported a catalytic enantioselective cyanosilylation of ketones using a chiral oxazaborolidinium ion: Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384. In addition, our group found that the gadolinium catalyst derived from 37 is effective in catalytic enantioselective conjugate addition of cyanide: Mita, T.; Sasaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 514.