FIRST ENANTIOSELECTIVE SYNTHESIS OF MIKANECIC ACID VIA DIELS-ALDER CYCLOADDITION MEDIATED CONSTRUCTION OF CHIRAL VINYLIC QUATERNARY CENTER

被引：32
|
作者：
BASAVAIAH, D
PANDIARAJU, S
SARMA, PKS
机构：
[1] School of Chemistry, University of Hyderabad, Hyderabad
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 24期
关键词：
D O I：
10.1016/S0040-4039(00)73158-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral mikanecic acid (1) was synthesized in 74% enantiomeric purity (92% ee after crystallization) via asymmetric Diels-Alder reaction of a novel in situ generated chiral 1,3-butadiene-2-carboxylate (A).
引用
收藏
页码：4227 / 4230
页数：4
相关论文
共 50 条
  • [1] Enantioselective Diels-Alder cycloaddition by preorganization on a chiral Lewis acid template
    Bienaymé, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) : 2670 - 2673
  • [2] Enantioselective Construction of Octahydroquinolines via Trienamine-Mediated Diels-Alder Reactions
    Inoshita, Taichi
    Goshi, Kei
    Morinaga, Yuka
    Umeda, Yuhei
    Ishikawa, Hayato
    ORGANIC LETTERS, 2019, 21 (08) : 2903 - 2907
  • [3] Highly enantioselective chiral anion-mediated Diels-Alder cycloadditions
    Yoon, Tehshik P.
    Allen, Charles P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [4] Studies on the synthesis of gymnodimine. Construction of the spiroimine portion via Diels-Alder cycloaddition
    White, JD
    Wang, GQ
    Quaranta, L
    ORGANIC LETTERS, 2003, 5 (26) : 4983 - 4986
  • [5] Synthesis of a taxinine analog via the intramolecular Diels-Alder cycloaddition
    Tetrahedron Lett, 45 (8069):
  • [6] Synthesis of a taxinine analog via the intramolecular Diels-Alder cycloaddition
    Winkler, JD
    Bhattacharya, SK
    Batey, RA
    TETRAHEDRON LETTERS, 1996, 37 (45) : 8069 - 8072
  • [7] ENANTIOSELECTIVE CONSTRUCTION OF HIGHLY FUNCTIONALIZED BICYCLO[4.3.0] SYSTEM THROUGH DIELS-ALDER CYCLOADDITION
    FUJI, K
    TANAKA, K
    ABE, H
    ITOH, A
    NODE, M
    TAGA, T
    MIWA, Y
    SHIRO, M
    TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1319 - 1327
  • [8] Catalytic enantioselective Diels-Alder reaction via a chiral indium(III) complex
    Teo, YC
    Loh, TP
    ORGANIC LETTERS, 2005, 7 (13) : 2539 - 2541
  • [9] Enantioselective Synthesis of Allenylenol Silyl Ethers via Chiral Lithium Amide Mediated Reduction of Ynenoyl Silanes and Their Diels-Alder Reactions
    Sasaki, Michiko
    Kondo, Yasuhiro
    Moto-ishi, Ta-ichi
    Kawahata, Masatoshi
    Yamaguchi, Kentaro
    Takeda, Kei
    ORGANIC LETTERS, 2015, 17 (05) : 1280 - 1283
  • [10] IRIDOIDS - ENANTIOSELECTIVE SYNTHESIS OF LOGANIN VIA AN ASYMMETRIC DIELS-ALDER REACTION
    VANDEWALLE, M
    VANDEREYCKEN, J
    OPPOLZER, W
    VULLIOUD, C
    TETRAHEDRON, 1986, 42 (14) : 4035 - 4043
12345