Z-SELECTIVE OLEFINATION OF BASE-SENSITIVE CHIRAL BETA-HYDROXY-ALPHA-AMINOALDEHYDES USING A MODIFIED HORNER-WADSWORTH-EMMONS REACTION

Authors
RUBSAM F EVERS AM MICHEL C GIANNIS A
Citation
F. Rubsam et al., Z-SELECTIVE OLEFINATION OF BASE-SENSITIVE CHIRAL BETA-HYDROXY-ALPHA-AMINOALDEHYDES USING A MODIFIED HORNER-WADSWORTH-EMMONS REACTION, Tetrahedron, 53(5), 1997, pp. 1707-1714
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
5
Year of publication
1997
Pages
1707 - 1714
Database
ISI
SICI code
0040-4020(1997)53:5<1707:ZOOBCB>2.0.ZU;2-3
Abstract
The HWE reaction of base-sensitive chiral beta-hydroxy-alpha-aminoalde hydes (serinals) was achieved under mild conditions with complete Z-se lectivity using bis(trifluoroethyl) phosphonates and LiCl, DBU in THF. The use of the corresponding dimethyl phosphonates resulted in a mixt ure off and Z-configurated products, the ratio of which was found to d epend on the size of the ester group. (C) 1997, Elsevier Science Ltd.