TY - JOUR
T1 - Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide
AU - Davies, Stephen G.
AU - Epstein, Simon W.
AU - Garner, A. Christopher
AU - Ichihara, Osamu
AU - Smith, Andrew D.
PY - 2002/8/1
Y1 - 2002/8/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0036675535&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(02)00406-8
DO - 10.1016/S0957-4166(02)00406-8
M3 - Article
AN - SCOPUS:0036675535
SN - 0957-4166
VL - 13
SP - 1555
EP - 1565
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 14
ER -