New procedures for the resolution of chiral tert-butylphenylphosphine oxide and some of its reactions

被引:71
作者
Drabowicz, J
Lyzwa, P
Omelanczuk, J
Pietrusiewicz, KM
Mikolajczyk, M
机构
[1] Polish Acad Sci, Ctr Mol & Macromol Studies, PL-90363 Lodz, Poland
[2] Marie Curie Sklodowska Univ, Dept Organ Chem, PL-20614 Lublin, Poland
关键词
D O I
10.1016/S0957-4166(99)00264-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Racemic t-butylphenylphosphine oxide was resolved via formation of diastereoisomeric complexes with (+)-(R)-1,1'-binaphthalene-2,2'-diol and (+)-(S)-mandelic acid. With the latter complexing agent, separation of the essentially enantiopure (-)-(S)-enantiomer was achieved in a single complexation process. Addition of paraformaldehyde to this enantiomer gave alpha-hydroxymethyl-t-butylphenylphosphine oxide with high stereoselectivity and retention of configuration at phosphorus while its reaction with methyl bromoacetate in methanol/sodium methoxide resulted in the formation of methyl t-butylphenylphosphinate with inversion at phosphorus. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2757 / 2763
页数:7
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