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

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 14期

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.

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页码：2757 / 2763

页数：7

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