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Volumn 8, Issue 24, 2006, Pages 5509-5512

Efficient asymmetric synthesis of quaternary (E)-vinylglycines by deconjugative alkylation of dehydroamino acids

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINO ACID; DRUG DERIVATIVE; GLYCINE; UNCLASSIFIED DRUG; VINYLGLYCINE;

EID: 33845964996     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062162r     Document Type: Article
Times cited : (27)

References (34)
  • 5
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    • For reviews of synthetic approaches to quaternary amino acids, see: a
    • For reviews of synthetic approaches to quaternary amino acids, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3517-3599
    • Cativiela, C.1    Diaz-de-Villegas, M.D.2
  • 8
    • 33646507896 scopus 로고    scopus 로고
    • Other synthetic approaches to quaternary (E)-vinylglycines include: (a) sigmatropic rearrangement: Armstrong, A.; Challinor, L.; Cooke, R. S.; Moir, J. H.; Treweeke, N. R. J. Org. Chem. 2006, 71, 4028-4030.
    • Other synthetic approaches to quaternary (E)-vinylglycines include: (a) sigmatropic rearrangement: Armstrong, A.; Challinor, L.; Cooke, R. S.; Moir, J. H.; Treweeke, N. R. J. Org. Chem. 2006, 71, 4028-4030.
  • 10
    • 0141854368 scopus 로고    scopus 로고
    • Addition of alkenylzirconocenes to a α-imino esters: Wipf, P.; Stephenson, C. R. J. Org. Lett. 2003, 5, 2449-2452.
    • (b) Addition of alkenylzirconocenes to a α-imino esters: Wipf, P.; Stephenson, C. R. J. Org. Lett. 2003, 5, 2449-2452.
  • 11
    • 0037958740 scopus 로고    scopus 로고
    • Strecker reaction: Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634-5635.
    • (c) Strecker reaction: Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634-5635.
  • 12
    • 0035939145 scopus 로고    scopus 로고
    • Self-regeneration of stereocenters approach from vinylglycine: Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343.
    • (d) Self-regeneration of stereocenters approach from vinylglycine: Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343.
  • 14
    • 0030907412 scopus 로고    scopus 로고
    • Vinylation of alanine enolates: Ma, D.; Ma, Z.; Jian, J.; Yang, Z.; Zheng, C. Tetrahedron: Asymmetry 1997, 8, 889-893.
    • (e) Vinylation of alanine enolates: Ma, D.; Ma, Z.; Jian, J.; Yang, Z.; Zheng, C. Tetrahedron: Asymmetry 1997, 8, 889-893.
  • 16
    • 37049086701 scopus 로고    scopus 로고
    • Alkylation of styrylglycine enolates: Chang, C.-J.; Fang, J.-M.; Lee, G.-H.; Wang, Y. J. Chem. Soc., Perkin Trans. 1 1994, 3587-3593. See also ref 9.
    • (f) Alkylation of styrylglycine enolates: Chang, C.-J.; Fang, J.-M.; Lee, G.-H.; Wang, Y. J. Chem. Soc., Perkin Trans. 1 1994, 3587-3593. See also ref 9.
  • 18
    • 0019974058 scopus 로고
    • For related studies, see: a
    • For related studies, see: (a) Hoppe, I.; Schöllkopf, U. Synthesis 1982, 129-131.
    • (1982) Synthesis , pp. 129-131
    • Hoppe, I.1    Schöllkopf, U.2
  • 20
    • 29044432963 scopus 로고    scopus 로고
    • For alkylations of dienediolates leading to quaternary α-hydroxy acids, see: a
    • For alkylations of dienediolates leading to quaternary α-hydroxy acids, see: (a) Newton, R.; Marsden, S. P. Synthesis 2005, 3263-3270.
    • (2005) Synthesis , pp. 3263-3270
    • Newton, R.1    Marsden, S.P.2
  • 27
    • 0002325951 scopus 로고
    • Additionally, the trimethyl phosphonoglycinate derivative is commercially available Aldrich
    • (b) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53-60. Additionally, the trimethyl phosphonoglycinate derivative is commercially available (Aldrich).
    • (1984) Synthesis , pp. 53-60
    • Schmidt, U.1    Lieberknecht, A.2    Wild, J.3
  • 30
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    • See Supporting Information for details
    • See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.