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Volumn 40, Issue 43, 1999, Pages 7713-7716

An alkylidene carbene C-H insertion strategy for the enantioselective synthesis of α,α-dialkyl-α-amino acids

Author keywords

, Dialkyl amino acid; Alkylidene carbene; C H insertion; Enantioselective

Indexed keywords

2,5 METHANOLEUCINE; ALKYL GROUP; AMINO ACID DERIVATIVE; CYCLOPENTENE DERIVATIVE; KETONE; UNCLASSIFIED DRUG;

EID: 0033595854     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01613-5     Document Type: Article
Times cited : (26)

References (20)
  • 3
  • 4
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    • (c) Takahashi, A.; Naganawa, H.; Ikeda, D.; Okami, Y. Tetrahedron 1991, 47, 3621. Total synthesis: Kende, A. S.; Liu, K.; Jos Brands, K. M. J. Am. Chem. Soc. 1995, 117, 10597.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10597
    • Kende, A.S.1    Liu, K.2    Jos Brands, K.M.3
  • 9
    • 0030955088 scopus 로고    scopus 로고
    • and references cited therein
    • For a recent review, see: Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225, and references cited therein.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 225
    • Wirth, T.1
  • 11
    • 0000223506 scopus 로고
    • The singlet/triplet energy gap has been determined to be 48 kcal/mol for vinylidene carbene itself: Wu, C. J.; Carter, E. A. J. Phys. Chem. 1991, 95, 8352;
    • (1991) J. Phys. Chem. , vol.95 , pp. 8352
    • Wu, C.J.1    Carter, E.A.2
  • 13
    • 0001676885 scopus 로고
    • but this also appears to be an under-developed area of research
    • Doyle has recently shown that rhodium carbeniods can be used to generate nitrogen-bearing quaternary stereocentres: Doyle, M. P.; Kalinin, A. V. Synlett 1995, 1075, but this also appears to be an under-developed area of research.
    • (1995) Synlett , pp. 1075
    • Doyle, M.P.1    Kalinin, A.V.2
  • 18
    • 0009752022 scopus 로고    scopus 로고
    • note
    • The presence of NOE enhancements between both protons on the C1 hydroxymethylene group and the C3 proton of 16 confirmed the relative stereochemistry of this compound as shown below. (equation presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.