Studies on lactams .102. Environ-friendly approaches to densely functionalized beta-lactams

被引:47
作者
Jayaraman, M [1 ]
Manhas, MS [1 ]
Bose, AK [1 ]
机构
[1] STEVENS INST TECHNOL,DEPT CHEM & CHEM ENGN,HOBOKEN,NJ 07030
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(96)02421-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient approach to densely functionalized alpha-allyl-beta-lactams has been developed using organometallic reagents and alpha-keto-beta-lactams. Indium mediated Barbier reaction in aqueous media proceeded with a higher level of diastereoselectivity and chemical yield than zinc mediated Barbier reaction in anhydrous organic solvents. (C) 1997, Elsevier Science Ltd.
引用
收藏
页码:709 / 712
页数:4
相关论文
共 19 条
  • [1] Microwave-assisted rapid synthesis of alpha-amino-beta-lactams
    Bose, AK
    Jayaraman, M
    Okawa, A
    Bari, SS
    Robb, EW
    Manhas, MS
    [J]. TETRAHEDRON LETTERS, 1996, 37 (39) : 6989 - 6992
  • [2] A NOVEL CHEMICAL TRANSFORMATION OF 3-VINYL-4-SUBSTITUTED-2-AZETIDINONES - STUDIES ON LACTAMS .77.
    BOSE, AK
    KRISHNAN, L
    WAGLE, DR
    MANHAS, MS
    [J]. TETRAHEDRON LETTERS, 1986, 27 (49) : 5955 - 5958
  • [3] CINTAS P, 1995, SYNLETT, P1087
  • [4] GEORG GI, 1992, ORGANIC CHEM BETA LA, P299
  • [5] ISAAC MB, 1995, TETRAHEDRON LETT, V36, P8957
  • [6] Diastereoselective addition of grignard reagents to azetidine-2,3-dione: Synthesis of novel Taxol(R) analogues
    Kant, J
    Schwartz, WS
    Fairchild, C
    Gao, Q
    Huang, S
    Long, BH
    Kadow, JF
    Langley, DR
    Farina, V
    Vyas, D
    [J]. TETRAHEDRON LETTERS, 1996, 37 (36) : 6495 - 6498
  • [7] Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications
    Li, CJ
    [J]. TETRAHEDRON, 1996, 52 (16) : 5643 - 5668
  • [8] ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION
    LI, CJ
    [J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2023 - 2035
  • [9] MANHAS MS, 1988, HETEROCYCLES, V27, P1755
  • [10] MANHAS MS, 1976, HETEROCYCLES, V5, P699