title: Asymmetric conjugate addition of Grignard reagents to 3-silyl unsaturated esters for the facile preparation of enantioenriched β-silylcarbonyl compounds and allylic silanes.
abstract: A highly enantioselective conjugate addition of Grignard reagents to 3-silyl unsaturated esters to deliver synthetically useful chiral β-silylcarbonyl compounds was developed. The synthetic value of this methodology was further illustrated by the synthesis of enantioenriched β-hydroxyl esters and the facile access granted to various α-chiral allylic silanes. A plethora of diastereoselective transformations of β-silylenolates were also investigated and afforded manifold organosilanes that contained contiguous stereogenic centers with excellent enantioselectivity.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65) 67911961.
authors.forename: Kai
authors.initials: K
authors.lastname: Zhao
authors.forename: Teck-Peng
authors.initials: TP
authors.lastname: Loh
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D007202:Indicators and Reagents; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D004952:Esters; D007202:Indicators and Reagents; D012821:Silanes
keywords: Grignard reagents; Michael addition; asymmetric synthesis; domino reactions; organosilanes