A CONVENIENT, STEREODIVERGENT APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF N-BOC-AMINOALKYL EPOXIDES

Authors
CASTEJON P PASTO M MOYANO A PERICAS MA RIERA A
Citation
P. Castejon et al., A CONVENIENT, STEREODIVERGENT APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF N-BOC-AMINOALKYL EPOXIDES, Tetrahedron letters, 36(17), 1995, pp. 3019-3022
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
17
Year of publication
1995
Pages
3019 - 3022
Database
ISI
SICI code
0040-4039(1995)36:17<3019:ACSATT>2.0.ZU;2-W
Abstract
An efficient, stereodivergent and enantioselective synthesis of N-Boc- aminoalkyl epoxides has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-diols, and after a change in the nitrogen protecting group, an intramolecular Mitsunobu reaction leads to the erythro aminoalkyl epoxides; a three step sequence consi sting of protection of the primary alcohol, activation of the secondar y alcohol and simultaneous deprotection/cyclization affords in good yi elds the corresponding three isomers.