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-diphenylphosphinoyl-1- phenylpentan-3-one

Peter O'Brien, Harold R. Powell, Paul R. Raithby, Stuart Warren

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29 Citations (Scopus)

Abstract

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°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.

Original languageEnglish
Pages (from-to)1031-1039
Number of pages9
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number7
DOIs
Publication statusPublished - 7 Apr 1997

ASJC Scopus subject areas

  • Chemistry(all)

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