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Volumn 130, Issue 39, 2008, Pages 13145-13151

Sequential C-Si bond formations from diphenylsilane: Application to silanediol peptide isostere precursors

Author keywords

[No Author keywords available]

Indexed keywords

BOND FORMATION; CHEMOSELECTIVE; DIASTEREOSELECTIVE ADDITIONS; DIPEPTIDE; DIPHENYLSILANE; LITHIUM METALS; OPTICALLY ACTIVE; PROTEASE INHIBITOR; PROTEOLYTIC ENZYME; RADICAL INITIATORS; SEQUENTIAL FUNCTIONALIZATION; SILICON BONDS; TWO-STEP ASSEMBLY; WILKINSON'S CATALYST;

EID: 58149165245     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804720p     Document Type: Article
Times cited : (78)

References (64)
  • 11
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    • (2002) Science of Synthesis , vol.4
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  • 30
    • 0033484573 scopus 로고    scopus 로고
    • For a review, see: c
    • For a review, see: (c) Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25-35.
    • (1999) Chem. Soc. Rev , vol.28 , pp. 25-35
    • Roberts, B.P.1
  • 32
    • 0025766611 scopus 로고    scopus 로고
    • Diphenylsilane has been reported to yield only the monoalkylated product in a silyl radical addition to an α,β-unsaturated ester, see: Smadja, W, Zahouily, M, Journet, M, Malacria, M. Tetrahedron Lett. 1991, 32, 3683-3686
    • Diphenylsilane has been reported to yield only the monoalkylated product in a silyl radical addition to an α,β-unsaturated ester, see: Smadja, W.; Zahouily, M.; Journet, M.; Malacria, M. Tetrahedron Lett. 1991, 32, 3683-3686.
  • 40
    • 67650514695 scopus 로고
    • Patai, S, Rappoport, Z, Eds, Wiley: New York
    • Ojima, I. In The Chemistry of organic silicon compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Part 2, pp 1504-1508.
    • (1989) The Chemistry of organic silicon compounds , Issue.PART 2 , pp. 1504-1508
    • Ojima, I.1
  • 41
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    • Not unexpectedly, it appears electronic factors play a major role in controlling regioselectivity as attempts to apply n-butylacrylate in this protocol gave 46% of the Markovnikov product selectively, and acrylonitrile and N-tert-butylacrylamide also gave the Markovikov product, however only in trace amounts.
    • Not unexpectedly, it appears electronic factors play a major role in controlling regioselectivity as attempts to apply n-butylacrylate in this protocol gave 46% of the Markovnikov product selectively, and acrylonitrile and N-tert-butylacrylamide also gave the Markovikov product, however only in trace amounts.
  • 44
    • 0029471604 scopus 로고
    • For a more recent review, see for example: c
    • For a more recent review, see for example: (c) Lickiss, P. D.; Smith, C. M. Coord. Chem. Rev. 1995, 145, 75-124.
    • (1995) Coord. Chem. Rev , vol.145 , pp. 75-124
    • Lickiss, P.D.1    Smith, C.M.2
  • 52
    • 20844461105 scopus 로고    scopus 로고
    • For selected examples of the use of this chiral sulfinimine, see: a
    • For selected examples of the use of this chiral sulfinimine, see: (a) Brinner, K. M.; Ellman, J. A. Org. Biomol. Chem. 2005, 3, 2109.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 2109
    • Brinner, K.M.1    Ellman, J.A.2
  • 60
    • 67650521520 scopus 로고    scopus 로고
    • In accordance with notions mentioned in ref 21c
    • In accordance with notions mentioned in ref 21c.
  • 64
    • 67650545338 scopus 로고    scopus 로고
    • Aa represents any natural or non-natural amino acid
    • Aa represents any natural or non-natural amino acid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.