Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate

Authors
Stoncius, A Mast, CA Sewald, N
Citation
A. Stoncius et al., Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate, TETRAHEDR-A, 11(19), 2000, pp. 3849-3853
Citations number
10
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
19
Year of publication
2000
Pages
3849 - 3853
Database
ISI
SICI code
0957-4166(20001006)11:19<3849:CODDIT>2.0.ZU;2-B
Abstract
The conjugate addition of methylcuprates and methyllithium to ethyl 5-pheny l-1,3-dioxolan-4-yl-2-propenoate was investigated. It was found that the st ereoselectivity is highly dependent on the reagent used. In reactions with stabilized methylcuprates, the anti-1,4-addition product is mainly formed, whereas syn-diastereoselectivity is observed in the reaction with methyllit hium. Additions of methyllithium were optimized with respect to solvent and additives. (C) 2000 Elsevier Science Ltd. All rights reserved.