(S)-2-(Dibenzylamino)-3-phenylpropanal as a chiral auxiliary: A new strategy for the asymmetric synthesis of 2-substituted alcohols

Jonathan Clayden*, Catherine McCarthy, John G. Cumming

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

21 Citations (Scopus)

Abstract

The high levels of 1,2-stereocontrol observed in nucleophilic additions to (S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from L-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along-with the (S)-2- (dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols beating oxygen- or carbon-based 2-substituents.

Original languageEnglish
Pages (from-to)1427-1440
Number of pages14
JournalTetrahedron: Asymmetry
Volume9
Issue number8
DOIs
Publication statusPublished - 24 Apr 1998

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