Catalytic asymmetric hydrosilylation of butadiynes: A new synthesis of optically active allenes

被引：32
|
作者：
Tillack, A [1 ]
Michalik, D [1 ]
Koy, C [1 ]
Michalik, M [1 ]
机构：
[1] Univ Rostock eV, Inst Organ Katalyseforsch, D-18055 Rostock, Germany
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 36期
关键词：
asymmetric hydrosilylation; butadiynes; chiral allenes; rhodium phosphine complexes;
D O I：
10.1016/S0040-4039(99)01403-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Rh-catalyzed hydrosilylation of butadiynes to chiral allenes in the presence of chiral phosphine ligands is described. For the first time an enantiomeric excess of 22% was achieved using PPM ligand ((2S,4S)-(-)-4-(diphenylphosphino)-2-(diphenylphosphinomethyl)-pyrrolidine). (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：6567 / 6568
页数：2
相关论文
共 50 条
  • [1] A new asymmetric synthesis of optically active allenes via metal catalyzed hydrosilylation
    Tillack, A
    Koy, C
    Michalik, D
    Fischer, C
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (01) : 116 - 121
  • [2] Catalytic Asymmetric Synthesis of Optically Active Allenes from Terminal Alkynes
    Ye, Juntao
    Li, Suhua
    Chen, Bo
    Fan, Wu
    Kuang, Jinqiang
    Liu, Jinxian
    Liu, Yu
    Miao, Bukeyan
    Wan, Baoqiang
    Wang, Yuli
    Xie, Xi
    Yu, Qiong
    Yuan, Weiming
    Ma, Shengming
    ORGANIC LETTERS, 2012, 14 (05) : 1346 - 1349
  • [3] Optically active allenes from β-lactone templates:: Asymmetric total synthesis of (-)-malyngolide
    Wan, ZH
    Nelson, SG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) : 10470 - 10471
  • [4] Synthesis of new optically active phosphine ligands and their use in catalytic asymmetric reactions
    Imamoto, T
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1998, 56 (06) : 511 - 520
  • [5] Study in the catalytic asymmetric synthesis of optically active organophosphate triesters
    Wei, Tzyh-Mann
    Nakayama, Kensaku
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [6] CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALCOHOLS VIA HYDROSILYLATION OF OLEFINS WITH A CHIRAL MONOPHOSPHINE-PALLADIUM CATALYST
    HAYASHI, T
    UOZUMI, Y
    PURE AND APPLIED CHEMISTRY, 1992, 64 (12) : 1911 - 1916
  • [7] Recent advances in catalytic asymmetric synthesis of allenes
    Chu, Wen-Dao
    Zhang, Yan
    Wang, Jianbo
    CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (20) : 4570 - 4579
  • [8] ASYMMETRIC CATALYSIS .29. OPTICALLY-ACTIVE PRIMARY AMINES BY ENANTIOSELECTIVE CATALYTIC HYDROSILYLATION OF KETOXIMES
    BRUNNER, H
    BECKER, R
    GAUDER, S
    ORGANOMETALLICS, 1986, 5 (04) : 739 - 746
  • [9] NEW ASYMMETRIC SYNTHESIS OF OPTICALLY-ACTIVE SILANES
    RICHTER, WJ
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 169 (01) : 9 - 17
  • [10] STUDIES ON THE CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE MEDICINES
    ACHIWA, K
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1995, 115 (09): : 681 - 699
12345