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Volumn 8, Issue 10, 2006, Pages 2127-2130

Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROSULFONYL ISOCYANATE; ISOCYANIC ACID DERIVATIVE; LACTAM; SILANE DERIVATIVE;

EID: 33744773513     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060596g     Document Type: Article
Times cited : (37)

References (41)
  • 4
    • 0034625424 scopus 로고    scopus 로고
    • For reviews of N-acyliminium ion chemistry, see: (a) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817-3856.
    • (2000) Tetrahedron , vol.56 , pp. 3817-3856
    • Speckamp, W.N.1    Moolenaar, M.J.2
  • 18
    • 0002237394 scopus 로고
    • Synthesis of α-siloxy allylic silanes was achieved by the protection of α-hydroxy allylic silanes. Numerous reports have been published for the synthesis of α-hydroxy allylic silanes: (a) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
    • (1974) Acc. Chem. Res. , vol.7 , pp. 77-84
    • Brook, A.G.1
  • 27
    • 33744731204 scopus 로고    scopus 로고
    • note
    • The stereochemistry of (S)-1 was assigned by analogy. See ref 12a. The stereochemistry of the lactam (+)-2 was assigned utilizing the accepted [3+2] annulation mechanism. For the mechanism of the [3+2] annulation, see ref 7a.
  • 34
    • 0000880626 scopus 로고
    • and references therein
    • Laube, T. Acc. Chem. Res. 1995, 28, 399-405 and references therein.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 399-405
    • Laube, T.1
  • 39
    • 33744778810 scopus 로고    scopus 로고
    • note
    • The stereochemistry of γ-lactam 25 was confirmed by X-ray crystallography and nOe studies. The stereochemistry of all other substituted γ-lactams were proven by nOe studies.
  • 41
    • 33744720464 scopus 로고    scopus 로고
    • note
    • The benzhydryldimethylsilyl group led to better oxidation yields as compared to the cumyldimethylsilyl group.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.