Substrate-Controlled Michael Additions of Chiral Ketones to Enones
- 25 November 2014
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 16 (23) , 6220-6223
Abstract
Substrate-controlled Michael additions of the titanium(IV) enolate of lactate-derived ketone 1 to acyclic α,β-unsaturated ketones in the presence of a Lewis acid (TiCl4 or SnCl4) provide the corresponding 2,4-anti-4,5-anti dicarbonyl compounds in good yields and excellent diastereomeric ratios. Likely, the nucleophilic species involved in such additions are bimetallic enolates that may add to enones through cyclic transition states. Finally, further studies indicate that a structurally related β-benzyloxy chiral ketone can also participate in such stereocontrolled conjugate additions.Keywords
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