CHELATION CONTROLLED ALDOL REACTION OF TETRONIC ACID DIANION WITH KETONES

被引:7
作者
HONDA, T
KONDOH, H
OKUYAMA, A
HAYAKAWA, T
TSUBUKI, M
NAGASE, H
机构
[1] Institute of Medicinal Chemistry, Hoshi University, Shinagawa-ku, Tokyo, 142
关键词
D O I
10.3987/COM-91-S18
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chelation effect in the aldol reaction of dianion of tetronic acid with ketones was investigated to give the erythro adduct, predominantly, via the six-membered chelation transition state. The carbon-carbon bond formation occurred at the 5-position siteselectively in this reaction.
引用
收藏
页码:67 / 72
页数:6
相关论文
共 8 条
  • [1] EVANS DA, 1983, TOP STEREOCHEM, V13, P1
  • [2] Heathcock C. H., 1984, COMPREHENSIVE CARB B, V5B, P177
  • [3] HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, pCH2
  • [4] HONDA T, 1991, CHEM PHARM BULL, V39, P1866
  • [5] ONE-STEP STEREOCHEMICAL DETERMINATION OF CONTIGUOUS 4 ACYCLIC CHIRAL CENTERS ON THE STEROIDAL SIDE-CHAIN - A NOVEL SYNTHESIS OF BRASSINOLIDE
    KAMETANI, T
    KATOH, T
    TSUBUKI, M
    HONDA, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) : 7055 - 7060
  • [6] MUKAIYAMA T, 1982, ORG REACTIONS, V28, P203
  • [7] SYNTHETIC ROUTES TO THE PIPEROLIDES, FADYENOLIDES, EPOXYPIPEROLIDES, AND RELATED-COMPOUNDS
    PELTER, A
    ALBAYATI, RIH
    AYOUB, MT
    LEWIS, W
    PARDASANI, P
    HANSEL, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (04): : 717 - 742
  • [8] CHELATION OR NON-CHELATION CONTROL IN ADDITION-REACTIONS OF CHIRAL ALPHA-ALKOXY AND BETA-ALKOXY CARBONYL-COMPOUNDS
    REETZ, MT
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08): : 556 - 569