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

Journal article

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. © 2002 Elsevier Science Ltd. All rights reserved.

Authors: Davies, S; Epstein, S; Garner, A; Ichihara, O; Smith, A

• Publication status: Published
• Journal: TETRAHEDRON-ASYMMETRY
• Volume: 13
• Issue: 14
• Pages: 1555-1565
• Publication date: 2002-08-01
• DOI: 10.1016/S0957-4166(02)00406-8
• ISSN: 0957-4166
• Language: English