Asymmetric Conjugate Addition of Grignard Reagents to 3-Silyl Unsaturated Esters for the Facile Preparation of Enantioenriched β-Silylcarbonyl Compounds and Allylic Silanes

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

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.

Original languageEnglish
Pages (from-to)16764-16772
Number of pages9
JournalChemistry - A European Journal
Volume20
Issue number50
DOIs
StatePublished - 8 Dec 2014
Externally publishedYes

Keywords

  • Grignard reagents
  • Michael addition
  • asymmetric synthesis
  • domino reactions
  • organosilanes

Fingerprint

Dive into the research topics of 'Asymmetric Conjugate Addition of Grignard Reagents to 3-Silyl Unsaturated Esters for the Facile Preparation of Enantioenriched β-Silylcarbonyl Compounds and Allylic Silanes'. Together they form a unique fingerprint.

Cite this