Memory of chirality effects in aldol cyclisations of 1-(3-oxobutyryl) derivatives of L-4-oxaproline and L-proline isopropyl esters

被引:22
作者
Brewster, AG
Jayatissa, J
Mitchell, MB
Schofield, A
Stoodley, RJ
机构
[1] UMIST, Dept Chem, Manchester M60 1QD, Lancs, England
[2] Astra Zeneca Pharmaceut, Macclesfield SK10 4TG, Cheshire, England
[3] Roche Discovery Welwyn, Welwyn Garden City AL7 3AY, Herts, England
基金
英国工程与自然科学研究理事会;
关键词
aldol reactions; amino acid derivatives; asymmetric induction; oxazolidines; pyrrolidines; pyrrolinones;
D O I
10.1016/S0040-4039(02)00632-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoretentive C C bond formations are features of the aldol cyclisations of the 1-(3-oxobutyryl) derkratives of L-4-oxaproline and L-proline isopropyl esters. consistent with the involvement of axially chiral enolate intermediates. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3919 / 3922
页数:4
相关论文
共 27 条
  • [1] Andrews MD, 1997, SYNTHESIS-STUTTGART, P305
  • [2] Regioselective Dieckmann cyclisations leading to enantiopure highly functionalised tetramic acid derivatives
    Andrews, MD
    Brewster, AG
    Crapnell, KM
    Ibbett, AJ
    Jones, T
    Moloney, MG
    Prout, K
    Watkin, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02): : 223 - 235
  • [3] HIDDEN AXIAL CHIRALITY AS A STEREODIRECTING ELEMENT IN REACTIONS INVOLVING ENOL(ATE) INTERMEDIATES .1. CYCLIZATION REACTIONS OF METHYL (4R)-3-(2-DIAZO-3-OXOBUTANOYL)THIAZOLIDINE-4-CARBOXYLATE AND RELATED-COMPOUNDS
    BEAGLEY, B
    BETTS, MJ
    PRITCHARD, RG
    SCHOFIELD, A
    STOODLEY, RJ
    VOHRA, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (15): : 1761 - 1770
  • [4] 'Hidden' axial chirality as a stereodirecting element in reactions involving enol(ate) intermediates.: Part 2.: Cyclisation reactions of methyl (4R)-3-(2-diazo-3-oxobutanoyl)-1,1-dioxo-1λ6,3- (and 1-oxo-1λ4,3-) thiazolidine-4-carboxylates
    Betts, MJ
    Pritchard, RG
    Schofield, A
    Stoodley, RJ
    Vohra, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08): : 1067 - 1072
  • [5] BEULSHAUSEN T, 1992, LIEBIGS ANN CHEM, P523
  • [6] Stereoselective intramolecular aldol reactions of (4R)-3-(3-oxobutanoyl)-1,3-thiazolidine-4-carboxylates believed to be directed by 'self-induced' axial chirality
    Brewster, AG
    Frampton, CS
    Jayatissa, J
    Mitchell, MB
    Stoodley, RJ
    Vohra, S
    [J]. CHEMICAL COMMUNICATIONS, 1998, (03) : 299 - 300
  • [7] Conformational memory in enantioselective radical reductions and a new radical clock reaction
    Buckmelter, AJ
    Kim, AI
    Rychnovsky, SD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) : 9386 - 9390
  • [8] Stereoselective synthesis of quaternary α-amino acids.: Part 2.: Cyclic compounds
    Cativiela, C
    Díaz-de-Villegas, MD
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (03) : 645 - 732
  • [9] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds
    Cativiela, C
    Diaz-de-Villegas, MD
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (20) : 3517 - 3599
  • [10] THE STEREOCHEMISTRY OF AN OXAZOLINE DERIVATIVE OF THREONINE - IMPROVEMENT OF A RECENT THREONINE SYNTHESIS
    ELLIOTT, DF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1949, (MAR): : 589 - 594