Enantioselective synthesis of phospholanes using chiral lithium amide desymmetrisation

被引:12
作者
Blake, AJ [1 ]
Hume, SC [1 ]
Li, WS [1 ]
Simpkins, NS [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
基金
英国工程与自然科学研究理事会;
关键词
asymmetric synthesis; chiral lithium amide; phospholane;
D O I
10.1016/S0040-4020(02)00366-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective deprotonation of 1,2,5-triphenylphospholane oxide with a chiral base, followed by electrophilic quenching, gives a range of chiral products in good yield and in ca. 85% ee. The absolute and relative configuration of two of the products was determined by X-ray crystallography. A number of the chiral phospholane oxides were subjected to further transformations, in particular reduction to give enantiomerically pure phospholanes. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:4589 / 4602
页数:14
相关论文
共 21 条
  • [1] The asymmetric synthesis of phosphorus- and sulfur-containing tricarbonyl(η6-arene)chromium complexes using the chiral base approach
    Ariffin, A
    Blake, AJ
    Ewin, RA
    Li, WS
    Simpkins, NS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (21): : 3177 - 3189
  • [2] APPLICATION OF HOMOCHIRAL LITHIUM AMIDE BASE CHEMISTRY TO A THIANE OXIDE SYSTEM
    ARMER, R
    BEGLEY, MJ
    COX, PJ
    PERSAD, A
    SIMPKINS, NS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (24): : 3099 - 3104
  • [3] Concerning the synthesis and enantioselective rearrangements of episulfoxides
    Blake, AJ
    Cooke, PA
    Kendall, JD
    Simpkins, NS
    Westaway, SM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (02): : 153 - 163
  • [4] BUNN BJ, 1993, J CHEM SOC P1, V32, P3113
  • [5] Modular phospholane ligands in asymmetric catalysis
    Burk, MJ
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 363 - 372
  • [6] ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES
    COX, PJ
    SIMPKINS, NS
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (01) : 1 - 26
  • [7] ON ENANTIOSELECTIVE DEPROTONATION - SYNTHESIS AND CRYSTAL-STRUCTURE OF A CHIRAL AMIDOLITHIUM TETRAHYDROFURAN COMPLEX
    EDWARDS, AJ
    HOCKEY, S
    MAIR, FS
    RAITHBY, PR
    SNAITH, R
    SIMPKINS, NS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) : 6942 - 6943
  • [8] PREPARATION OF OPTICALLY PURE 1,2,5-TRIPHENYLPHOSPHOLANE - USE AS LIGAND FOR ENANTIOSELECTIVE TRANSITION-METAL CATALYSIS
    FIAUD, JC
    LEGROS, JY
    [J]. TETRAHEDRON LETTERS, 1991, 32 (38) : 5089 - 5092
  • [9] Guillen F, 1997, B SOC CHIM FR, V134, P371
  • [10] HORNER L, 1965, TETRAHEDRON LETT, V33, P1157