REVERSAL OF THE STEREOCHEMICAL COURSE OF THE ADDITION OF PHENYLMAGNESIUM BROMIDE TO N-BENZYLIMINES DERIVED FROM R-GLYCERALDEHYDE DEPENDING ON THE O-PROTECTING GROUP AND ITS APPLICATION TO THE SYNTHESIS OF BOTHENANTIOMERS OF PHENYLGLYCINE

Authors
BADORREY R CATIVIELA C DIAZDEVILLEGAS MD GALVEZ JA
Citation
R. Badorrey et al., REVERSAL OF THE STEREOCHEMICAL COURSE OF THE ADDITION OF PHENYLMAGNESIUM BROMIDE TO N-BENZYLIMINES DERIVED FROM R-GLYCERALDEHYDE DEPENDING ON THE O-PROTECTING GROUP AND ITS APPLICATION TO THE SYNTHESIS OF BOTHENANTIOMERS OF PHENYLGLYCINE, Tetrahedron, 53(4), 1997, pp. 1411-1416
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
4
Year of publication
1997
Pages
1411 - 1416
Database
ISI
SICI code
0040-4020(1997)53:4<1411:ROTSCO>2.0.ZU;2-#
Abstract
The N-Benzyl imines derived from 2,3-di-O-benzyl-D-glyceraldehyde and 2,3-di-O-isopropylidene-D-glyceraldehyde reacted with phenylmagnesium bromide to afford fully protected aminodiols with total diastereoselec tivity. The stereochemical course of the addition reaction depends on the nature of the O-protecting group. These compounds can be easily tr ansformed to enantiomerically pure (R) and (S)alpha-phenylglycine. (C) 1997, Elsevier Science Ltd.