Stereochemical course of the hydrogen migration in the boron trifluoride etherate-catalyzed rearrangement of 1,1-disubstituted epoxides

Authors
Hara, N Mochizuki, A Tatara, A Fujimoto, Y
Citation
N. Hara et al., Stereochemical course of the hydrogen migration in the boron trifluoride etherate-catalyzed rearrangement of 1,1-disubstituted epoxides, TETRAHEDR-A, 11(9), 2000, pp. 1859-1868
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
9
Year of publication
2000
Pages
1859 - 1868
Database
ISI
SICI code
0957-4166(20000519)11:9<1859:SCOTHM>2.0.ZU;2-O
Abstract
Mechanistic studies on the BF3.Et2O-catalyzed rearrangement of optically ac tive, regioselectively deuterated 1,1-disubstituted epoxides to aldehydic p roducts revealed that the two hydrogens migrate at the migration terminus w ith opposite stereochemical preferences, i.e. the hydrogen anti to the bulk y substituent prefers to migrate with inversion of configuration, whereas t he hydrogen syn to the bulky substituent prefers to migrate with retention of configuration. (C) 2000 Elsevier Science Ltd. All rights reserved.