Addition of enantiomerically pure amines to activated olefines - II. On the addition to ethyl (E)-4-oxo-4-phenyl-2-butenoate

Citation
M. Knollmuller et al., Addition of enantiomerically pure amines to activated olefines - II. On the addition to ethyl (E)-4-oxo-4-phenyl-2-butenoate, MONATS CHEM, 130(6), 1999, pp. 769-782
Citations number
25
Categorie Soggetti
Chemistry
Journal title
MONATSHEFTE FUR CHEMIE
ISSN journal
00269247 → ACNP
Volume
130
Issue
6
Year of publication
1999
Pages
769 - 782
Database
ISI
SICI code
0026-9247(199906)130:6<769:AOEPAT>2.0.ZU;2-D
Abstract
The addition of (S)-phenethylamine to ethyl (E)-4-oxo-3-phenyl-2-butenoate shows no kinetic selectivity, whereas - according to the b,pl,ti-rule - the AB- and BE-product are kinetically preferred in the addition of (S)-alanin e-isopropylester and -benzylester, respectively. Ln the reaction of benzyl (S)-alaninate, contrary to the other and earlier examined examples no therm odynamic preference for the BB-product over the AB-product was observed.