Stereoselective preparation of functionalized tertiary P-chiral phosphine oxides by nucleophilic addition of lithiated tert-butylphenylphosphine oxide to carbonyl compounds.

被引：50
|
作者：
Haynes, RK
Lam, WWL
Yeung, LL
机构：
[1] Department of Chemistry, Hong Kong Univ. of Sci. and Technol., Kowloon, Clear Water Bay Road
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 27期
关键词：
D O I：
10.1016/0040-4039(96)00952-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nucleophilic carbonyl and conjugate addition reactions of configurationally stable lithiated P-chiral tert-butylphenylphosphine oxide with aldehydes and alpha,beta-unsaturated carbonyl compounds occur in good yields with diastereoselectivities ranging from 33 to greater than or equal to 98%. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：4729 / 4732
页数：4
相关论文
共 3 条
  • [1] A direct synthesis of P-chiral phosphine boranes via dynamic resolution of lithiated racemic tert-butylphenylphosphine-borane with (-)-sparteine
    Wolfe, B
    Livinghouse, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (20) : 5116 - 5117
  • [2] Preparation of Optically Pure Tertiary Phosphine Oxides via the Addition of P-Stereogenic Secondary Phosphine Oxide to Activated Alkenes
    Wang, Ji-Ping
    Nie, Shao-Zhen
    Zhou, Zhong-Yang
    Ye, Jing-Jing
    Wen, Jing-Hong
    Zhao, Chang-Qiu
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17): : 7644 - 7653
  • [3] Completely stereoselective P-C bond formation via base-induced [1,3]- and [1,2]-intramolecular rearrangements of aryl phosphinates, phosphinoamidates and related compounds:: generation of P-chiral β-hydroxy, β-mercapto- and α-amino tertiary phosphine oxides and phosphine sulfides
    Au-Yeung, TL
    Chan, KY
    Haynes, RK
    Williams, ID
    Yeung, LL
    TETRAHEDRON LETTERS, 2001, 42 (03) : 457 - 460
1