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Volumn 44, Issue 19, 2005, Pages 2896-2899

Direct organocatalytic and highly enantio- and diastereoselective mannich reactions of α-substituted α-cyanoacetates

Author keywords

Asymmetric catalysis; Diastereoselectivity; Enantioselectivity; Mannich bases; Organocatalysis

Indexed keywords

DIASTERSELECTIVITY; METAL-FREE CATALYSIS; ORGANOCATALYSTS; STEREOCENTERS;

EID: 18844456337     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500144     Document Type: Article
Times cited : (156)

References (73)
  • 2
    • 0032482080 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 1044-1070;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1044-1070
  • 3
    • 0000733768 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, Chap. 4.1
    • b) E. F. Kleinmann in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, Chap. 4.1.
    • (1991) Comprehensive Organic Synthesis , vol.2
    • Kleinmann, E.F.1
  • 4
    • 10844266525 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • For reviews on Mannich reactions with preformed enolates see: a) S. Kobayashi, M. Ueno in Comprehensive Asymmetric Catalysis, Supplement, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2004, pp. 143-150;
    • (2004) Comprehensive Asymmetric Catalysis, Supplement , vol.1 , pp. 143-150
    • Kobayashi, S.1    Ueno, M.2
  • 6
    • 0001059120 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • c) S. E. Denmark, O. J.-C. Nicaise in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 923-961;
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 923-961
    • Denmark, S.E.1    Nicaise, O.J.-C.2
  • 7
    • 1642415515 scopus 로고    scopus 로고
    • for direct Mannich reactions, see: d) A. Córdova, Acc. Chem. Res. 2004, 37, 102-112;
    • (2004) Acc. Chem. Res. , vol.37 , pp. 102-112
    • Córdova, A.1
  • 12
    • 0035902842 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 2995-2997.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2995-2997
  • 13
    • 11144263200 scopus 로고    scopus 로고
    • For general reviews on organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286;
    • (2004) Angew. Chem. , vol.116 , pp. 5248-5286
    • Dalko, P.I.1    Moisan, L.2
  • 14
    • 6044269452 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 5138-5175
  • 18
    • 0035886887 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 3726-3748.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3726-3748
  • 21
    • 4544387566 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 4476-4478;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4476-4478
  • 26
    • 0042969372 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 3677-3680;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3677-3680
  • 37
    • 18844461913 scopus 로고    scopus 로고
    • (Eds.: H.-G. Schmalz, T. Wirth), Wiley-VCH, Weinheim
    • d) C. Carter, A. Nelson in Organic Synthesis Highlights V (Eds.: H.-G. Schmalz, T. Wirth), Wiley-VCH, Weinheim, 2003, pp. 125-133;
    • (2003) Organic Synthesis Highlights V , pp. 125-133
    • Carter, C.1    Nelson, A.2
  • 40
  • 53
    • 0141725892 scopus 로고    scopus 로고
    • refs. [8a,b,d]
    • For successful examples, see: b) M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11204-11205; refs. [8a,b,d];
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11204-11205
    • Taylor, M.S.1    Jacobsen, E.N.2
  • 57
    • 0037541354 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1688-1690;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1688-1690
  • 60
    • 18844408590 scopus 로고    scopus 로고
    • note
    • Changing the imine ester group (Me, Et, nPr, iPr, tBu) gave enantioselectivities for the preferred diastereomer above 90% ee. The d.r. ranged between 80:20-89:11, the highest value having been observed for ethyl.
  • 63
    • 0141630824 scopus 로고    scopus 로고
    • The carbamate-protected imine was prepared in situ following the procedure developed by Kobayashi and co-workers; see: a) Y. Nakamura, R. Matsubara, H. Kiyohara, S. Kobayashi, Org. Lett. 2003, 5, 2481-2484;
    • (2003) Org. Lett. , vol.5 , pp. 2481-2484
    • Nakamura, Y.1    Matsubara, R.2    Kiyohara, H.3    Kobayashi, S.4
  • 65
    • 84985239895 scopus 로고
    • The synthesis and use of α-bromo glycine derivatives in the preparation of acyl α-imino esters was initially developed by Steglich and co-workers; see: c) R. Kober, W. Steglich, Liebigs Ann. Chem. 1983, 599-609;
    • (1983) Liebigs Ann. Chem. , pp. 599-609
    • Kober, R.1    Steglich, W.2
  • 67
    • 4544294700 scopus 로고    scopus 로고
    • For a discussion of the difficulties in the deprotection of tosyl amines, see: R. R. Milburn, V. Snieckus, Angew. Chem. 2004, 116, 910-912;
    • (2004) Angew. Chem. , vol.116 , pp. 910-912
    • Milburn, R.R.1    Snieckus, V.2
  • 69
    • 18844391988 scopus 로고    scopus 로고
    • note
    • As noted (Table 2) the reactions were performed on a 0.1-mmol scale. Compound 3h was also prepared on a 0.5-mmol scale under the optimized conditions with similar results [95 % yield, 85:15 (u/l), and 95% ee].
  • 70
    • 0000803537 scopus 로고
    • The terms u (unlike) and l (like) were introduced by Seebach and Prelog as a general way of designating relative configurations in molecules with several chiral centers, particularly those in which terms like syn/anti or erythro/threo are not easily adopted; see: D. Seebach, V. Prelog, Angew. Chem. 1982, 94, 696;
    • (1982) Angew. Chem. , vol.94 , pp. 696
    • Seebach, D.1    Prelog, V.2
  • 72
    • 18844408048 scopus 로고    scopus 로고
    • see refs. [8b,d]
    • Up to 61:39 (d.r.) and up to 51 % ee. This fact has also been observed in other cinchona alkaloid-catalyzed reactions of α-substituted cyanoacetates; see refs. [8b,d].
  • 73
    • 18844378865 scopus 로고    scopus 로고
    • CCDC 260994 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.