DIASTEREOSELECTIVE PERACID EPOXIDATION - CONTROL OF THE FACE SELECTIVITY VIA FUNCTIONAL-GROUP TUNING AND PROPER CHOICE OF EPOXIDATION REAGENT

Authors
JENSEN AJ LUTHMAN K
Citation
Aj. Jensen et K. Luthman, DIASTEREOSELECTIVE PERACID EPOXIDATION - CONTROL OF THE FACE SELECTIVITY VIA FUNCTIONAL-GROUP TUNING AND PROPER CHOICE OF EPOXIDATION REAGENT, Tetrahedron letters, 39(20), 1998, pp. 3213-3214
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
20
Year of publication
1998
Pages
3213 - 3214
Database
ISI
SICI code
0040-4039(1998)39:20<3213:DPE-CO>2.0.ZU;2-7
Abstract
Peracid epoxidation of 1a-f with 3-chloroperbenzoic acid (m-CPBA) and trifluoroperacetic acid (CF3CO3H) show different stereoselectivities. The olefins are substituted with two directing groups which are expect ed to direct the peracid to opposite faces of the alkene. Optimal face selectivities could be achieved by the proper choice of directing gro ups and epoxidation reagent. (C) 1998 Elsevier Science Ltd. All rights reserved.