Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

Stephen G. Davies*, Simon W. Epstein, A. Christopher Garner, Osamu Ichihara, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

An efficient protocol for the transformation of homochiral α-hydroxy-β-amino esters to their α-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino 1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-α-methylbenzyl protected α-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the α-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides α-amino acids in 94-98% e.e.

Original languageEnglish
Pages (from-to)1555-1565
Number of pages11
JournalTetrahedron Asymmetry
Volume13
Issue number14
DOIs
Publication statusPublished - 1 Aug 2002

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