CONJUGATE ADDITION OF CHLORIDE TO ALPHA,BETA-UNSATURATED CHIRAL IMIDES PROMOTED BY BCL3-DERIVATIVES .2.

Authors
CARDILLO G DIMARTINO E GENTILUCCI L TOMASINI C TOMASONI L
Citation
G. Cardillo et al., CONJUGATE ADDITION OF CHLORIDE TO ALPHA,BETA-UNSATURATED CHIRAL IMIDES PROMOTED BY BCL3-DERIVATIVES .2., Tetrahedron : asymmetry, 6(8), 1995, pp. 1957-1963
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
8
Year of publication
1995
Pages
1957 - 1963
Database
ISI
SICI code
0957-4166(1995)6:8<1957:CAOCTA>2.0.ZU;2-F
Abstract
The diastereoselective hydrochlorination of alpha,beta-unsaturated chi ral imides by reaction with BCl(2)OR or BCl(OR)(2) type reagents is de scribed. Complete diastereoselectivity is achieved through the use of new oxazolidin-2-ones ad hoc prepared for this purpose from (S)-trypto phan. An hypothesis on the donor-acceptor interactions, between the su bstrate and the Lewis acids, that drive the attack of the chloride pre ferentially to one face of the alkenoyl chain is reported.