Highly enantioselective cyanosilylation of aldehydes catalyzed by a Lewis acid-Lewis base bifunctional catalyst

被引:130
作者
Hamashima, Y [1 ]
Sawada, D [1 ]
Nogami, H [1 ]
Kanai, M [1 ]
Shibasaki, M [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
Lewis acid; Lewis base; asymmetric catalyst; cyanosilylation; epothilones;
D O I
10.1016/S0040-4020(00)01039-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new Bifunctional asymmetric catalyst containing a Lewis acid and a Lewis base (1) was developed and applied to the catalytic asymmetric cyanosilylation of aldehydes. The products were obtained generally with excellent enantiomeric excess. The experiments using the control catalyst (5) and the catalyst containing more electron-rich phosphine oxide (6) suggest that the catalyst I should promote the reaction via a dual activation of the aldehyde by the aluminum and TMSCN by the phosphine oxide. This reaction is practical and was applied to the catalytic asymmetric total synthesis of epothilone A. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:805 / 814
页数:10
相关论文
共 30 条
  • [1] The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes
    Belokon, YN
    Caveda-Cepas, S
    Green, B
    Ikonnikov, NS
    Krustalev, VN
    Larichev, VS
    Moscalenko, MA
    North, M
    Orizu, C
    Tararov, VI
    Tasinazzo, M
    Timofeeva, GI
    Yashkina, LV
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) : 3968 - 3973
  • [2] EFFENBERGER F, 1994, ANGEW CHEM INT EDIT, V33, P1555, DOI 10.1002/anie.199415551
  • [3] SYNTHESIS OF ANTIBACTERIAL PARA-QUINOLS FROM MARINE SPONGES - SYNTHETIC APPLICATIONS OF MASKED QUINONES
    EVANS, DA
    WONG, RY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (02) : 350 - 352
  • [4] CYANOSILYLATION OF ALDEHYDES AND KETONES - CONVENIENT ROUTE TO CYANOHYDRIN DERIVATIVES
    EVANS, DA
    TRUESDALE, LK
    CARROLL, GL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (02) : 55 - 56
  • [5] Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications
    Gregory, RJH
    [J]. CHEMICAL REVIEWS, 1999, 99 (12) : 3649 - 3682
  • [6] A new bifunctional asymmetric catalysis: An efficient catalytic asymmetric cyanosilylation of aldehydes
    Hamashima, Y
    Sawada, D
    Kanai, M
    Shibasaki, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) : 2641 - 2642
  • [7] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES CATALYZED BY CHIRAL SCHIFF-BASE TITANIUM ALKOXIDE COMPLEXES
    HAYASHI, M
    MIYAMOTO, Y
    INOUE, T
    OGUNI, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) : 1515 - 1522
  • [8] Enantioselective addition of trimethylsilyl cyanide to aldehydes induced by a new chiral Ti(IV) complex
    Hwang, CD
    Hwang, DR
    Uang, BJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) : 6762 - 6763
  • [9] A FACILE SYNTHESIS OF CYANOHYDRIN TRIMETHYLSILYL ETHERS BY THE ADDITION-REACTION OF TRIMETHYLSILYL CYANIDE WITH ALDEHYDES UNDER BASIC CONDITION
    KOBAYASHI, S
    TSUCHIYA, Y
    MUKAIYAMA, T
    [J]. CHEMISTRY LETTERS, 1991, (04) : 537 - 540
  • [10] CLEAVAGE REACTIONS OF TRIMETHYLSILYL CYANIDE - NEW SYNTHESIS OF O-(TRIMETHYLSILYL)-CYANOHYDRINES
    LIDY, W
    SUNDERME.W
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (02): : 587 - 593