AN ENANTIOSELECTIVE, STEREODIVERGENT SYNTHESIS OF THREONINE ANALOGS

Authors
DELLEMONACHE G DIGIOVANNI MC MISITI D ZAPPIA G
Citation
G. Dellemonache et al., AN ENANTIOSELECTIVE, STEREODIVERGENT SYNTHESIS OF THREONINE ANALOGS, Tetrahedron : asymmetry, 8(2), 1997, pp. 231-243
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
2
Year of publication
1997
Pages
231 - 243
Database
ISI
SICI code
0957-4166(1997)8:2<231:AESSOT>2.0.ZU;2-W
Abstract
An enantioselective and stereodivergent methodology for the synthesis of the four isomers of beta-hydroxy norvaline is presented starting fr om the common oxazolidin-2-one intermediate 1, via an iterative format ion of the oxazolidin-2-one ring to achieve the stereochemical control of the stereogenic centers. The flexibility of the present approach, for the synthesis of several threonine analogs, lies in the ready disp lacement of the sulfonate group in 2 with the Grignard reagents in the presence of CuI. (C) 1997 Elsevier Science Ltd.