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 language | English |
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Pages (from-to) | 16764-16772 |
Number of pages | 9 |
Journal | Chemistry - A European Journal |
Volume | 20 |
Issue number | 50 |
DOIs | |
State | Published - 8 Dec 2014 |
Externally published | Yes |
Keywords
- Grignard reagents
- Michael addition
- asymmetric synthesis
- domino reactions
- organosilanes