Origin of stereoselectivities in asymmetric alkoxyselenenylations

Authors
Wang, X Houk, KN Spichty, M Wirth, T
Citation
X. Wang et al., Origin of stereoselectivities in asymmetric alkoxyselenenylations, J AM CHEM S, 121(37), 1999, pp. 8567-8576
Citations number
48
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863 → ACNP
Volume
121
Issue
37
Year of publication
1999
Pages
8567 - 8576
Database
ISI
SICI code
0002-7863(19990922)121:37<8567:OOSIAA>2.0.ZU;2-I
Abstract
Asymmetric alkoxyselenenylations of alkenes have been studied by B3LYP/3-21 G, B3LYP/6-31G*, and SCI-PCM calculations. Stereoselectivities can be ratio nalized by the relative stabilities of transition states for attack of nucl eophiles on seleniranium intermediates. A model to explain and predict ster eoselectivities has been developed.