Investigation of the configurational stability of lithiated phosphine oxides using the Hoffmann test: X-ray structures of (2S(),3S(),4R())2-(N,N-dibenzylamino)-4-diphenylphosphinoyl-1-phenylpentan-3-ol and (2S(),4S(*))-2-(N,N-dibenzylamino)-4-diphenylphinoyl-1-phenylpentan-3-one

被引：21

作者：

OBrien, P ^{[1
]}

Powell, HR ^{[1
]}

Raithby, PR ^{[1
]}

Warren, S ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 07期

关键词：

D O I：

10.1039/a606720d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Hoffmann test (reaction of a racemic organolithium with a phenylalanine-derived aldehyde) is used to show that lithiated diphenylphosphine oxides are not configurationally stable in THF at -78 degrees C (usual reaction conditions) on the timescale of their rate of reaction with the aldehyde. The test is carried out by reacting lithiated ethyldiphenylphosphine oxide with a phenylalanine-derived aldehyde and because all four diastereoisomeric alcohols are obtained, it is necessary to determine the relative stereochemistry of the products. This is done using a combination of synthesis and X-ray crystallography of (2S*,3S*,4R*)-2-(N,N-dibenzylamino)-4-diphenylphosphinoyl-1-phenylpentan-3-ol and (2S*,4S*)-2-(N,N-dibenzylamino)-2-diphenylphosphinoyl-1-phenylpentan-3-one.

引用

页码：1031 / 1039

页数：9

共 70 条

[1] ENANTIOSELECTIVE TRANSFORMATIONS AND RACEMIZATION STUDIES OF HETEROATOM SUBSTITUTED ORGANOLITHIUM COMPOUNDS [J].