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

Autor:	Arvydas Stoncius, Norbert Sewald, Christian Alexander Mast
Rok vydání:	2000
Předmět:	Inorganic Chemistry Solvent chemistry.chemical_compound chemistry Reagent Organic Chemistry Organic chemistry Methyllithium Stereoselectivity Physical and Theoretical Chemistry Catalysis Conjugate
Zdroj:	Tetrahedron: Asymmetry. 11:3849-3853
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(00)00353-0
Popis:	The conjugate addition of methylcuprates and methyllithium to ethyl 5-phenyl-1,3-dioxolan-4-yl-2-propenoate was investigated. It was found that the stereoselectivity 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 methyllithium. Additions of methyllithium were optimized with respect to solvent and additives. (C) 2000 Elsevier Science Ltd. All rights reserved.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::901e4532b2c56ec1bf823747d294c846 https://doi.org/10.1016/s0957-4166(00)00353-0 Zobrazit plný text záznamu Full Text from ScienceDirect