About the stereoselectivity control in reactions of chiral ortho-sulfinyl benzyl carbanions with aldehydes

Autor:	José L. García Ruano, M. Teresa Aranda, Jose M. Aguirre
Rok vydání:	2004
Předmět:	Steric effects Aryl Organic Chemistry Sulfoxide Biochemistry Ethylbenzene chemistry.chemical_compound chemistry Drug Discovery Electronic effect Organic chemistry Epimer Stereoselectivity Carbanion
Zdroj:	Tetrahedron. 60:5383-5392
ISSN:	0040-4020
DOI:	10.1016/j.tet.2004.04.051
Popis:	Reactions of aliphatic and aromatic aldehydes with the benzyllithium derived from 2-p-tolylsulfinyl ethylbenzene yield mixtures of mainly two compounds, anti-3 and syn-4, epimers at hydroxylic carbon, easily separated by chromatography and desulfinylated into enantiomerically pure 1-alkyl (or aryl)-2-phenyl-1-propanols. The observed stereoselectivity at C(1) and C(2) is analyzed to the light of the steric and electronic effects of the substituents.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::49ad188f19ca0c46bf10abf98e726fe6 https://doi.org/10.1016/j.tet.2004.04.051 Zobrazit plný text záznamu Full Text from ScienceDirect