RELATIVE STEREOCONTROL IN AN INTRAMOLECULAR 4+3 CYCLOADDITION REACTION

被引：18
|
作者：
HARMATA, M
GAMLATH, CB
BARNES, CL
机构：
[1] Department of Chemistry, University of Missouri-Columbia, Columbia
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 02期
关键词：
D O I：
10.1016/S0040-4039(00)60563-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first complete study of relative stereocontrol in an intramolecular 4+3 cycloaddition has been performed. Thus, CH2Cl2 solutions of alkoxyallylic sulfones 5, 7, and 9 were treated with TiCl4 at -78-degrees-C to give diastereomeric cycloadducts in fair yield. For 5 and 7 diastereoselectivity was low, but suggested that allylic cation geometry plays a small but definitive role in determining the diastereomer distribution in the cycloadducts. For the cycloaddition reaction of 9, cation geometry is irrelevant and the cycloadduct is obtained in very high diastereomeric purity.
引用
收藏
页码：265 / 268
页数：4
相关论文
共 50 条
  • [41] Intermolecular [4+3] Cycloaddition of Cyclic Oxyallyl
    You Hong HU and Dong Lu BAI(Shanghai Inshtute of Materi Medica
    [J]. Chinese Chemical Letters, 1997, (07) : 563 - 564
  • [42] Asymmetric organocatalysis of 4+3 cycloaddition reactions
    Harmata, M
    Ghosh, SK
    Hong, XC
    Wacharasindhu, S
    Kirchhoefer, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) : 2058 - 2059
  • [43] Asymmetric catalytic [4+3] cycloaddition reactions
    Harmata, Michael
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) : 2297 - 2306
  • [44] STEREOCONTROL IN THE INTRAMOLECULAR NITRONE CYCLOADDITION TO VINYL SULFUR DERIVATIVES
    ANNUNZIATA, R
    CINQUINI, M
    COZZI, F
    GIARONI, P
    RAIMONDI, L
    [J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (04) : 251 - 264
  • [45] Induction of asymmetry on the [4+3] cycloaddition reaction of C2-functionalized furans
    Montaña, AM
    Grima, PM
    [J]. TETRAHEDRON LETTERS, 2002, 43 (11) : 2017 - 2021
  • [46] Fluorinated alcohol-mediated [4+3] cycloaddition reaction of indolyl alcohols with cyclopentadiene
    Liu, Jian
    Wang, Liang
    Wang, Xiaoxiao
    Xu, Lubin
    Hao, Zhihui
    Xiao, Jian
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (48) : 11510 - 11517
  • [47] INTRAMOLECULAR 4+3 CYCLOADDITIONS - THE SYNTHESIS OF CYCLOOCTANOIDS
    HARMATA, M
    ELAHMAD, S
    BARNES, CL
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 33 - ORGN
  • [48] Phosphine-catalyzed [4+3] cycloaddition reaction of aromatic azomethine imines with allenoates
    Li, Zhen
    Yu, Hao
    Feng, Yalin
    Hou, Zhanfeng
    Zhang, Lei
    Yang, Wenjun
    Wu, Yang
    Xiao, Yumei
    Guo, Hongchao
    [J]. RSC ADVANCES, 2015, 5 (43): : 34481 - 34485
  • [49] Dearomative Intramolecular (4+3) Cycloadditions of Thiophenes
    Zheng, Yufen
    Chen, Yueyao
    He, Yuxuan
    Rizzo, Antonio
    Zhou, Yuchen
    Low, Kam-Hung
    Krenske, Elizabeth H.
    Chiu, Pauline
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (33)
  • [50] The first transannular [4+3] cycloaddition reaction: synthesis of the ABCD ring structure of cortistatins
    Craft, Derek T.
    Gung, Benjamin W.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (41) : 5931 - 5934
12345