CYCLIC IMIDATE SALTS IN ACYCLIC STEREOCHEMISTRY - DIASTEREOSELECTIVE SYN-EPOXIDATION OF 2-ALKYL-4-ENAMIDES TO EPOXYAMIDES

Authors
MALIGRES PE WEISSMAN SA UPADHYAY V CIANCIOSI SJ REAMER RA PURICK RM SAGER J ROSSEN K ENG KK ASKIN D VOLANTE RP REIDER PJ
Citation
Pe. Maligres et al., CYCLIC IMIDATE SALTS IN ACYCLIC STEREOCHEMISTRY - DIASTEREOSELECTIVE SYN-EPOXIDATION OF 2-ALKYL-4-ENAMIDES TO EPOXYAMIDES, Tetrahedron, 52(9), 1996, pp. 3327-3338
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
9
Year of publication
1996
Pages
3327 - 3338
Database
ISI
SICI code
0040-4020(1996)52:9<3327:CISIAS>2.0.ZU;2-S
Abstract
Reaction of 2-alkyl-4-enamides with 1(+) and aqueous sodium bicarbonat e results in the diastereoselective formation of the corresponding iod ohydrins with essentially no iodolactone by-product. The reaction appe ars to proceed through a cyclic imidate type intermediate. This method ology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (ind inavir sulfate).