메뉴 건너뛰기




Volumn 43, Issue 34, 2004, Pages 4476-4478

Direct organocatalytic enantioselective mannich reactions of ketimines: An approach to optically active quaternary α -amino acid derivatives

Author keywords

Amino acids; Chiral amines; Mannich bases; Organocatalysis; Quaternary stereocenters

Indexed keywords

ALDEHYDES; AMINO ACIDS; CATALYSIS; STEREOCHEMISTRY;

EID: 4544387566     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460158     Document Type: Article
Times cited : (229)

References (46)
  • 1
    • 0000733768 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, chap. 4.1
    • For a review, see: a) E. F. Kleinmann in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, chap. 4.1, p. 893;
    • (1991) Comprehensive Organic Synthesis, Vol. 2 , vol.2 , pp. 893
    • Kleinmann, E.F.1
  • 3
    • 0032482080 scopus 로고    scopus 로고
    • b) M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096-1122; Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1044-1070
  • 14
    • 0035902842 scopus 로고    scopus 로고
    • e) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085; Angew. Chem. Int. Ed. 2001, 40, 2995-2997;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2995-2997
  • 16
    • 0034721440 scopus 로고    scopus 로고
    • For direct organocatalyzed enantioselective Mannich reactions of aldimines, see, for example: a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337;
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9336-9337
    • List, B.1
  • 27
    • 0042969372 scopus 로고    scopus 로고
    • k) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805-3808; Angew. Chem. Int. Ed. 2003, 42, 3677-3680;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3677-3680
  • 32
    • 0001227615 scopus 로고    scopus 로고
    • For recent reviews on the asymmetric construction of quaternary carbon centers, see: a) M. Cristoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
    • (2001) Angew. Chem. , vol.113 , pp. 4725-4732
    • Cristoffers, M.1    Mann, A.2
  • 33
    • 0035905575 scopus 로고    scopus 로고
    • For recent reviews on the asymmetric construction of quaternary carbon centers, see: a) M. Cristoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732; Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4591-4597
  • 35
    • 0032473509 scopus 로고    scopus 로고
    • b) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 388-401
  • 43
    • 4544226543 scopus 로고    scopus 로고
    • note
    • The ketimine 6, without intrinsic protecting-group anchoring, did not react with isovaleraldehyde (2a) in the presence of 5 mol% of L-proline (5a). (Diagram presented)
  • 45
    • 0034908567 scopus 로고    scopus 로고
    • For an example of the combination of protic acids and chiral diamines as the catalyst, see: S. Saito, M. Nakadai, H. Yamamoto, Synlett 2001, 1245-1248.
    • (2001) Synlett. , pp. 1245-1248
    • Saito, S.1    Nakadai, M.2    Yamamoto, H.3
  • 46
    • 4544245956 scopus 로고    scopus 로고
    • note
    • See also references [4f,n] for another approach of imines to a related enamine intermediate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.