Highly diastereoselective desymmetrizing intramolecular cyclization of allylstannane with a diketone promoted by Lewis acid or transition metal complex

被引：2
|
作者：
Shimada, T [1 ]
Asao, N [1 ]
Yamamoto, Y [1 ]
机构：
[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2001年 / 624卷 / 1-2期
关键词：
desymmetrizing cyclization; allylstannane; diketone; Lewis acid; transition metal catalyst;
D O I：
10.1016/S0022-328X(00)00897-4
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The Lewis acid mediated desymmetrizing intramolecular cyclization of prochiral allylstannyl diketone (1) gave a mixture of two diastereomers (2 and 3). Highly diastereoselective synthesis of each of the diastereomers was accomplished by appropriate choice of the Lewis acid. Compound 3 was also produced stereoselectively by using a palladium catalyst instead of Lewis acid. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码：136 / 142
页数：7
相关论文
共 37 条
  • [1] Lewis acid promoted highly diastereoselective desymmetric intramolecular cyclization of allylstannane with a diketone
    Shimada, T
    Yamamoto, Y
    TETRAHEDRON LETTERS, 1998, 39 (5-6) : 471 - 474
  • [2] Lewis Acid Promoted Highly Diastereoselective Desymmetric Intramolecular Cyclization of Allylstannane with a Diketone
    Shimada, T.
    Yamamoto, Y.
    Tetrahedron Letters, 39 (5-6):
  • [3] Highly diastereoselective Lewis acid promoted Claisen-Ireland rearrangement
    Koch, G
    Janser, P
    Kottirsch, G
    Romero-Giron, E
    TETRAHEDRON LETTERS, 2002, 43 (27) : 4837 - 4840
  • [4] Lewis acid-promoted diastereoselective radical cyclization using chiral α,β-unsaturated esters
    Nishida, M.
    Ueyama, E.
    Hayashi, H.
    Ohtake, Y.
    Yamaura, Y.
    Yanaginuma, E.
    Yonemitsu, O.
    Nishida, A.
    Kawakara, N.
    Journal of the American Chemical Society, 1994, 116 (14)
  • [5] Lewis acid mediated highly regioselective intramolecular cyclization for the synthesis of β-lapachone
    Bian, Jinlei
    Deng, Bang
    Zhang, Xiaojin
    Hu, Tianhan
    Wang, Nan
    Wang, Wei
    Pei, Haixiang
    Xu, Yu
    Chu, Hongxi
    Li, Xiang
    Sun, Haopeng
    You, Qidong
    TETRAHEDRON LETTERS, 2014, 55 (08) : 1475 - 1478
  • [6] LEWIS ACID-PROMOTED DIASTEREOSELECTIVE RADICAL CYCLIZATION USING CHIRAL ALPHA,BETA-UNSATURATED ESTERS
    NISHIDA, M
    UEYAMA, E
    HAYASHI, H
    OHTAKE, Y
    YAMAURA, Y
    YANAGINUMA, E
    YONEMITSU, O
    NISHIDA, A
    KAWAHARA, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) : 6455 - 6456
  • [7] Highly enantioselective Michael-cyclization cascade promoted by synergistic asymmetric aminocatalysis and Lewis acid catalysis
    Yu, Chenguang
    Zhang, Yinan
    Zhang, Shilei
    He, Jing
    Wang, Wei
    TETRAHEDRON LETTERS, 2010, 51 (13) : 1742 - 1744
  • [8] NEW METHODS FOR THE PREPARATION OF OPTICALLY-ACTIVE CARBOCYCLES - ASYMMETRIC ACETALIZATION AND LEWIS-ACID PROMOTED DIASTEREOSELECTIVE RADICAL CYCLIZATION
    NISHIDA, A
    NISHIDA, M
    YONEMITSU, O
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 44 - ORGN
  • [9] HIGH ASYMMETRIC INDUCTION IN LEWIS ACID-PROMOTED INTRAMOLECULAR ENE-TYPE REACTIONS - A DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (+)-A-ALLOKAINIC ACID
    OPPOLZER, W
    ROBBIANI, C
    BATTIG, K
    HELVETICA CHIMICA ACTA, 1980, 63 (07) : 2015 - 2018
  • [10] Lewis acid promoted intramolecular cyclization of (eta(4)-diene)Fe(CO)(3) complexes bearing functionalized side chains
    Yeh, MCP
    Chuang, LW
    Chang, SC
    Lai, ML
    Chou, CC
    ORGANOMETALLICS, 1997, 16 (20) : 4435 - 4444
1234