WITTIG REARRANGEMENT OF ALPHA-(PROPARGYLOXY)ALKYLLITHIUMS - PERISELECTIVITY AND STERIC COURSE AT THE LITHIUM-BEARING TERMINUS

Authors
TOMOOKA K KOMINE N NAKAI T
Citation
K. Tomooka et al., WITTIG REARRANGEMENT OF ALPHA-(PROPARGYLOXY)ALKYLLITHIUMS - PERISELECTIVITY AND STERIC COURSE AT THE LITHIUM-BEARING TERMINUS, Synlett, (9), 1997, pp. 1045-1046
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
9
Year of publication
1997
Pages
1045 - 1046
Database
ISI
SICI code
0936-5214(1997):9<1045:WROA-P>2.0.ZU;2-E
Abstract
The [2,3]-Wittig rearrangement of an enantiomerically defined alpha-pr opargyloxy stannane with butyllithium is shown to proceed with complet e inversion of configuration at the Li-bearing terminus. The periselec tivity ([2,3]- vs. [1,2]-) of the rearrangement depends markedly upon the nature of substituents on the acetylenic group.