| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5225535 | Tetrahedron | 2006 | 4 Pages |
Abstract
The hydroboration of acetophenone in the chiral solvent (S)-methyl lactate exhibits moderate enantioselectivities. A six-membered transition state involving the ketone, the borane, and the lactate as the only chiral source is proposed. Molecular modeling explains the experimentally observed enantioselectivities. Calculated ee-values are in accordance with those experimentally observed. Improved ee-values (up to 60%) can be obtained in the presence of stoichiometric amounts of Lewis acid at lower reaction temperatures.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Stefan H. Hüttenhain, Martin U. Schmidt, Fenja R. Schoepke, Magnus Rueping,