Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions

被引:227
作者
Groaning, MD [1 ]
Meyers, AI [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
D O I
10.1016/S0040-4020(00)00926-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chiral non-racemic bicyclic lactam has proven to be an exceptionally versatile chiral template for the asymmetric construction of a variety of optically pure compounds. Those lactams derived from keto acids have been applied to the synthesis of a host of natural products and pharmacologically interesting heterocycles and carbocycles. A variety of mechanistic questions regarding facial stereo-control have been investigated using the chiral template as the key probe. However, further elucidation of the subtle mechanistic principles involved await further study.
引用
收藏
页码:9843 / 9873
页数:31
相关论文
共 130 条
  • [1] CHIRAL PRECURSORS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE PIPERIDINES - TOTAL SYNTHESIS OF (R)-(-)-CONIINE
    AMAT, M
    LLOR, N
    BOSCH, J
    [J]. TETRAHEDRON LETTERS, 1994, 35 (14) : 2223 - 2226
  • [2] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine
    Amat, M
    Bosch, J
    Hidalgo, J
    Cantó, M
    Pérez, M
    Llor, N
    Molins, E
    Miravitlles, C
    Orozco, M
    Luque, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 3074 - 3084
  • [3] New chiral non-racemic piperidine-derived epoxy lactams
    Amat, M
    Llor, N
    Hidalgo, J
    Bosch, J
    Molins, E
    Miravitlles, C
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (09) : 2501 - 2504
  • [4] Preparation of enantiopure 6-(3-indolyl)-2-piperidones and conjugate additions to a 3,4-didehydro derivative
    Amat, M
    Llor, N
    Bosch, J
    Solans, X
    [J]. TETRAHEDRON, 1997, 53 (02) : 719 - 730
  • [5] Torsional and steric effects control the stereoselectivities of alkylations of pyrrolidinone enolates
    Ando, K
    Green, NS
    Li, Y
    Houk, KN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (22) : 5334 - 5335
  • [6] ASYMMETRIC CONJUGATE ADDITIONS TO CHIRAL BICYCLIC LACTAMS - A STEREOSELECTIVE, CONCISE SYNTHESIS OF CHIRAL 2-ALKYL-3,4-AZIRIDINOPYRROLIDINES
    ANDRES, CJ
    MEYERS, AI
    [J]. TETRAHEDRON LETTERS, 1995, 36 (20) : 3491 - 3494
  • [7] NON-METALLOCATALYZED EPOXIDATION OF CHIRAL UNSATURATED LACTAMS BY TERTIARY AMINE N-OXIDES
    ANDRES, CJ
    SPETSERIS, N
    NORTON, JR
    MEYERS, AI
    [J]. TETRAHEDRON LETTERS, 1995, 36 (10) : 1613 - 1616
  • [8] Asymmetric synthesis of the core cyclopentane of viridenomycin
    Arrington, MP
    Meyers, AI
    [J]. CHEMICAL COMMUNICATIONS, 1999, (15) : 1371 - 1372
  • [9] ASYMMETRIC-SYNTHESIS OF SPIRO 2-PYRROLIDIN-5-ONES AND 2-PIPERIDIN-6-ONES
    BAHAJAJ, AA
    BAILEY, PD
    MOORE, MH
    MORGAN, KM
    VERNON, JM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (21) : 2511 - 2512
  • [10] STRUCTURE RELATION OF CONJUGATED CYCLOALKENONES AND THEIR KETALS
    BECKER, D
    BRODSKY, NC
    KALO, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (13) : 2557 - 2562