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Volumn 45, Issue 43, 2006, Pages 7230-7233

A highly efficient and practical method for catalytic Asymmetric Vinylogous Mannich (AVM) reactions

Author keywords

Asymmetric catalysis; Enantioselective synthesis; Imines; Silver; Vinylogous Mannich reactions

Indexed keywords

AMINO ACIDS; CATALYSIS; SILVER; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 33751012442     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603496     Document Type: Article
Times cited : (139)

References (36)
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    • For a review of Mannich reactions, see
    • For a review of Mannich reactions, see: a) A. Córdova, Acc. Chem. Res. 2004, 37, 102-112;
    • (2004) Acc. Chem. Res. , vol.37 , pp. 102-112
    • Córdova, A.1
  • 7
    • 3042550754 scopus 로고    scopus 로고
    • for select recent reports of catalytic asymmetric Mannich reactions (not AVM), see: b) T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 7768-7769;
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 7768-7769
    • Hamada, T.1    Manabe, K.2    Kobayashi, S.3
  • 10
    • 16244364063 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1525-1529;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1525-1529
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    • Angew. Chem. Int. Ed. 2005, 44, 3600-3603;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3600-3603
  • 21
    • 33750974392 scopus 로고    scopus 로고
    • note
    • For determination of relative and absolute stereochemical identity of AVM products from reactions of 3, see the Supporting Information.
  • 22
    • 33750972816 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for all data.
  • 24
    • 0346162171 scopus 로고    scopus 로고
    • For a similar effect in Cr-catalyzed enantioselective aldol additions of siloxyfurans to aldehydes, see: S. Onitsuka, Y. Matsuoka, R. Irie, T. Katsuki, Chem. Lett. 2003, 32, 974-975.
    • (2003) Chem. Lett. , vol.32 , pp. 974-975
    • Onitsuka, S.1    Matsuoka, Y.2    Irie, R.3    Katsuki, T.4
  • 25
    • 33751019603 scopus 로고    scopus 로고
    • note
    • 2O (conditions in Table 1).
  • 26
    • 33750988150 scopus 로고    scopus 로고
    • note
    • Relative and absolute stereochemical identity of products derived from 5 was established through an X-ray crystal structure of 6j (entry 5, Table 2). See the Supporting Information for details.
  • 27
    • 33751006380 scopus 로고    scopus 로고
    • note
    • For relative and absolute stereochemical identity of products derived from 7, see the Supporting Information.
  • 28
    • 33750981464 scopus 로고    scopus 로고
    • note
    • 3N (synthesis of 4a with 1 mol% 1a, -78°C).
  • 29
    • 0034597491 scopus 로고    scopus 로고
    • Preference for endo-type ("Diels-Alder"-type) transition states has been suggested for diastereoselective (non-asymmetric) vinylogous Mannich reactions; see: S. K. Burr, S. F. Martin, Org. Lett. 2000, 2, 3445-3447.
    • (2000) Org. Lett. , vol.2 , pp. 3445-3447
    • Burr, S.K.1    Martin, S.F.2
  • 30
    • 33750993981 scopus 로고    scopus 로고
    • note
    • The C=N bond of chiral ligands do not undergo addition likely because of steric hinderance provided by the amino acid substituent.
  • 31
    • 15744387149 scopus 로고    scopus 로고
    • and references therein
    • Pre-association of the amide moiety with the siloxyfuran is also feasible; such an interaction would enhance enolsilane nucleophilicity and facilitate delivery; see: a) S. E. Denmark, G. L. Beutner, T. Wynn, M. D. Eastgate, J. Am. Chem. Soc. 2005, 127, 3774-3789, and references therein;
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 3774-3789
    • Denmark, S.E.1    Beutner, G.L.2    Wynn, T.3    Eastgate, M.D.4
  • 35
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    • Angew. Chem. Int. Ed. 2003, 42, 4244-4247.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4244-4247
  • 36
    • 33750972243 scopus 로고    scopus 로고
    • note
    • Preliminary results show that the present procedure is applicable to AVM of aldimines derived from aliphatic aldehydes.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.