Allyl sulfones as precursors to allylzincs in the palladium-catalyzed zinc-ene cyclization: Highly efficient synthesis of enantiopure (-)-erythrodiene

被引：37
|
作者：
Deng, K [1 ]
Chalker, J [1 ]
Yang, A [1 ]
Cohen, T [1 ]
机构：
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 17期
关键词：
D O I：
10.1021/ol051049i
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Easily prepared allyl phenyl sulfones, capable of introduction of the alkene by electrophilic alpha-substitution, are superior to allyl acetates as substrates for Pd-catalyzed Zn-ene cyclizations, providing C5 or C4N rings with cis-1,2-vinyl and -CH2Zn substituents. Several examples, with different methods of substrate preparation, are presented.
引用
收藏
页码：3637 / 3640
页数：4
相关论文
共 50 条
  • [1] PALLADIUM-CATALYZED INTRAMOLECULAR ZINC-ENE REACTIONS
    OPPOLZER, W
    SCHRODER, F
    TETRAHEDRON LETTERS, 1994, 35 (43) : 7939 - 7942
  • [2] New ethylzinc reagents with remarkable properties in palladium-catalyzed zinc-ene reactions
    Oppolzer, W
    Schroder, F
    Kahl, S
    HELVETICA CHIMICA ACTA, 1997, 80 (07) : 2047 - 2057
  • [3] Synthesis of (-)-α-Kainic Acid via TMSCl-Promoted Pd-Catalyzed Zinc-ene Cyclization of an Allyl Acetate
    Wei, Guoqing
    Chalker, Justin M.
    Cohen, Theodore
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19): : 7912 - 7917
  • [4] Allyl sulfones as precursors for Pd-catalyzed allylzincation. Natural product synthesis by intramolecular Zn-ene cyclization.
    Deng, K
    Cohen, T
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U191 - U191
  • [5] Palladium-catalyzed highly efficient synthesis of tetracenes and pentacenes
    Chen, Ming
    Chen, Yifeng
    Liu, Yuanhong
    CHEMICAL COMMUNICATIONS, 2012, 48 (100) : 12189 - 12191
  • [6] Synthesis of 3-alkylfuropyridines via palladium-catalyzed cyclization of iodopyridinyl allyl ethers
    Cho, SY
    Kim, SS
    Park, KH
    Kang, SK
    Choi, JK
    Hwang, KJ
    Yum, EK
    HETEROCYCLES, 1996, 43 (08) : 1641 - 1652
  • [7] Highly enantioselective palladium-catalyzed ene-type cyclization of a 1,6-enyne
    Hatano, M
    Terada, M
    Mikami, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (01) : 249 - 253
  • [8] Enantioselective Palladium-Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids
    Du, Kang
    Guo, Pan
    Chen, Yuan
    Cao, Zhen
    Wang, Zheng
    Tang, Wenjun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (10) : 3033 - 3037
  • [9] Highly efficient synthesis of cephalotaxine by two palladium-catalyzed cyclizations
    Tietze, LF
    Schirok, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (10): : 1124 - 1125
  • [10] Highly Efficient Synthesis of Cephalotaxine by Two Palladium-Catalyzed Cyclizations
    Institut für Organische Chemie, Universität, Tammannstrasse 2, D-37077 Göttingen, Germany
    Angew Chem (Int Ed Engl), 10 (1124-1125):
12345