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Volumn 11, Issue 18, 2009, Pages 4044-4047

Highly diastereoselective three-component vinylogous mannich reaction between isoquinolines, acyl/sulfonyl chlorides, and silyloxyfurans

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; SULFINIC ACID DERIVATIVE; SULFONYL CHLORIDE;

EID: 70349088637     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901452d     Document Type: Article
Times cited : (30)

References (52)
  • 1
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    • (2001) Prod. Rep. , vol.18 , pp. 148-170
    • Nat, B.K.W.1
  • 3
    • 0003780442 scopus 로고
    • Hansch, C., Sammes, P. G., Taylor, J. B., Eds.;Pergamon: Oxford
    • (c) Comprehensive Medicinal Chemistry, 1st ed.; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon: Oxford, 1990; Vol.3.
    • (1990) Comprehensive Medicinal Chemistry, 1st Ed. , vol.3
  • 5
    • 37049109717 scopus 로고
    • For examples and leading references, see: (a) Czarnocki, Z.; MacLean, D. B.; Szarek, W; J
    • For examples and leading references, see: (a) Czarnocki, Z.; MacLean, D. B.; Szarek, W; J, J. Chem. Soc., Chem. Commun. 1985, 1318-1319.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 1318-1319
  • 25
  • 33
    • 0035897085 scopus 로고    scopus 로고
    • For a review of the vinylogous Mannich reaction, see: (a)
    • For a review of the vinylogous Mannich reaction, see: (a) Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221-3242.
    • (2001) Tetrahedron , vol.57 , pp. 3221-3242
    • Bur, S.K.1    Martin, S.F.2
  • 45
    • 70349159334 scopus 로고    scopus 로고
    • 5 coupling constants for the major diastereomers were smaller (usually in the 4.8-5.8 Hz range) than for the minor diastereomer typically in the 6.5-8.0 Hz range). The same trends were observed in the vinylogous Mannich products for which X-ray crystal structures are not available, thereby allowing attribution of their relative stereochemistry.
    • 5 coupling constants for the major diastereomers were smaller (usually in the 4.8-5.8 Hz range) than for the minor diastereomer (typically in the 6.5-8.0 Hz range). The same trends were observed in the vinylogous Mannich products for which X-ray crystal structures are not available, thereby allowing attribution of their relative stereochemistry.
  • 46
    • 70349153681 scopus 로고    scopus 로고
    • While the absolute configuration of the major isomer of compound 5h has not yet been, determined with, certainty, the observation by Ohsawa (ref 7a) that the (S)-valine-derived chiral auxiliary gives the Mannich product having the R configuration at d of isoquinoline combined with our observation that the major product formed in the vinylogous Mannich reaction has the R*,R* configuration strongly suggests that 5h therefore has the R,R configuration
    • While the absolute configuration of the major isomer of compound 5h has not yet been, determined with, certainty, the observation by Ohsawa (ref 7a) that the (S)-valine-derived chiral auxiliary gives the Mannich product having the R configuration at d of isoquinoline combined with our observation that the major product formed in the vinylogous Mannich reaction has the R*,R* configuration strongly suggests that 5h therefore has the R,R configuration.
  • 47
    • 70349154063 scopus 로고    scopus 로고
    • γ of Si precludes use of the technique of ref 15 for attribution of the relative configuration
    • γ of Si precludes use of the technique of ref 15 for attribution of the relative configuration.
  • 49
    • 0034597491 scopus 로고    scopus 로고
    • An attempt to rationalize the diastereoselectivity observed in the vinylogous Mannich reaction between 2-methoxyfuran and an N-carbamoylpyrrolinium salt has been reported. See: Bur, S. K.; Martin, S. F.
    • An attempt to rationalize the diastereoselectivity observed in the vinylogous Mannich reaction between 2-methoxyfuran and an N-carbamoylpyrrolinium salt has been reported. See: Bur, S. K.; Martin, S. F. Org. Lett. 2000, 2, 3445-3447.
    • (2000) Org. Lett. , vol.2 , pp. 3445-3447
  • 51
    • 66449137290 scopus 로고    scopus 로고
    • For leading references, see: (a)
    • For leading references, see: (a) Stearman, C. J.; Wilson, M.; Padwa, A. J. Org. Chem. 2009, 74, 3491-3499.
    • (2009) , vol.74 , pp. 3491-3499
    • Stearman, C.J.1    Wilson, M.2    Org Chem, P.A.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.