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Volumn , Issue 18, 2008, Pages 3061-3064

Chirality transfer from epoxide to carbanion: Base-induced alkylation of O-carbamoyl cyanohydrins of β-silyl-α,β-epoxy aldehyde

Author keywords

Alkylation; Asymmetric synthesis; Carbanions; Chirality; Rearrangement

Indexed keywords


EID: 53749100438     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800300     Document Type: Article
Times cited : (17)

References (42)
  • 14
    • 0036135888 scopus 로고    scopus 로고
    • For α-nitrile carbanions, see: a
    • For α-nitrile carbanions, see: a) F. F. Fleming, B. C. Shook, Tetrahedron 2002, 58, 1-23;
    • (2002) Tetrahedron , vol.58 , pp. 1-23
    • Fleming, F.F.1    Shook, B.C.2
  • 20
    • 0035835953 scopus 로고    scopus 로고
    • For the use of the Brook rearrangement in tandem bond-formation strategies, see: d
    • For the use of the Brook rearrangement in tandem bond-formation strategies, see: d) W. H. Moser, Tetrahedron 2001, 57, 2065-2084.
    • (2001) Tetrahedron , vol.57 , pp. 2065-2084
    • Moser, W.H.1
  • 23
    • 0003152616 scopus 로고
    • Eds, A. R. Katritzky, O. Meth-Cohn, C. W. Rees, C. J. Moody, Pergamon, Oxford
    • g) H. Qi, D. P. Curran in Comprehensive Organic Functional Group Transformations (Eds.: A. R. Katritzky, O. Meth-Cohn, C. W. Rees, C. J. Moody), Pergamon, Oxford, 1995, pp. 409-431;
    • (1995) Comprehensive Organic Functional Group Transformations , pp. 409-431
    • Qi, H.1    Curran, D.P.2
  • 27
    • 53749083638 scopus 로고    scopus 로고
    • This compound (94%ee) was prepared from 7 according to the procedure described in the literature.[3b
    • [3b]
  • 30
    • 53749083774 scopus 로고    scopus 로고
    • 1H NMR spectrum of the crude product mixture, as they were inseparable. The ee of (Z)-11 was determined by chiral HPLC analysis with a chiral column.
    • 1H NMR spectrum of the crude product mixture, as they were inseparable. The ee of (Z)-11 was determined by chiral HPLC analysis with a chiral column.
  • 31
    • 53749097561 scopus 로고    scopus 로고
    • was obtained from the reaction of 10b with NaHMDS in THF as the sole product in 89% yield
    • rac-(E)-11 was obtained from the reaction of 10b with NaHMDS in THF as the sole product in 89% yield.
    • rac-(E , vol.11
  • 33
    • 34147107497 scopus 로고    scopus 로고
    • Carlier has recently reported that magnesiated cyclopropyl nitrile anions possess macroscopic configurational stability. P. R. Carlier, Y. Zhang, Org. Lett. 2007, 9, 1319-1322
    • Carlier has recently reported that magnesiated cyclopropyl nitrile anions possess macroscopic configurational stability. P. R. Carlier, Y. Zhang, Org. Lett. 2007, 9, 1319-1322.
  • 38
    • 53749097421 scopus 로고    scopus 로고
    • We have tried to prepare cyanohydrin derivatives of α,β- unsaturated aldehydes, but O-carbamoylation of the cyanohydrin gave back the starting aldehyde
    • We have tried to prepare cyanohydrin derivatives of α,β- unsaturated aldehydes, but O-carbamoylation of the cyanohydrin gave back the starting aldehyde.
  • 41
    • 53749097149 scopus 로고    scopus 로고
    • The absolute configuration of 18 was not determined.
    • The absolute configuration of 18 was not determined.
  • 42
    • 53749098123 scopus 로고    scopus 로고
    • We believe that the ee values are meaningful because they were reproducible
    • We believe that the ee values are meaningful because they were reproducible.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.