Highly enantioselective allylation of arylaldehydes catalyzed by a silver(I)-chiral binaphthylthiophosphoramide

被引:25
作者
Wang, CJ [1 ]
Shi, M [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
allylation; N; S ligands; silver; asymmetric catalysis; aldehydes;
D O I
10.1002/ejoc.200300099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral diphenylthiophosphoramide L2 prepared from diphenylthiophosphinic chloride and (R)-(+)-N-ethyl-1,1'-binaphthyl-2,2'-diamine 2 was used as a Catalytic chiral ligand in the silver(1)-catalyzed enantioselective allylation reaction of arylaldehydes with allyltributyltin to furnish high ee (up to 98%) of the homoallylic alcohols. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
引用
收藏
页码:2823 / 2828
页数:6
相关论文
共 27 条
  • [1] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX
    AOKI, S
    MIKAMI, K
    TERADA, M
    NAKAI, T
    [J]. TETRAHEDRON, 1993, 49 (09) : 1783 - 1792
  • [2] Arai Y, 1995, CHEM PHARM BULL, V43, P2243
  • [3] CATALYTIC ENANTIOSELECTIVE C-C COUPLING - ALLYL TRANSFER AND MUKAIYAMA ALDOL REACTION
    BACH, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (04): : 417 - 419
  • [4] CRYSTAL AND MOLECULAR-STRUCTURES OF (1,8-BIS(2-PYRIDYL)-3,6-DITHIAOCTANE)COPPER(I) HEXAFLUOROPHOSPHATE AND PERCHLORATO(1,8-BIS(2-PYRIDYL)-3,6-DITHIAOCTANE)COPPER(II) PERCHLORATE - STEREODYNAMICS OF THE COPPER(II)-COPPER(I) COUPLE
    BRUBAKER, GR
    BROWN, JN
    YOO, MK
    KINSEY, RA
    KUTCHAN, TM
    MOTTEL, EA
    [J]. INORGANIC CHEMISTRY, 1979, 18 (02) : 299 - 302
  • [5] CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS
    COSTA, AL
    PIAZZA, MG
    TAGLIAVINI, E
    TROMBINI, C
    UMANIRONCHI, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 7001 - 7002
  • [6] Lewis base activation of Lewis acids: Catalytic enantioselective allylation and propargylation of aldehydes
    Denmark, SE
    Wynn, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) : 6199 - 6200
  • [7] ASYMMETRIC ALLYLATION OF ALDEHYDES WITH CHIRAL LEWIS-BASES
    DENMARK, SE
    COE, DM
    PRATT, NE
    GRIEDEL, BD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6161 - 6163
  • [8] FURUTA K, 1991, SYNLETT, P561
  • [9] Gawley R.E., 1996, PRINCIPLES ASYMMETRI
  • [10] Hoveyda AH, 1996, ANGEW CHEM INT EDIT, V35, P1263