Enolate generation under hydrogenation conditions: catalytic aldol cycloreduction of keto-enones |
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Authors: | Huddleston Ryan R Krische Michael J |
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Affiliation: | Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA. |
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Abstract: | [reaction: see text] Formal heterolytic activation of elemental hydrogen under Rh catalysis enables the reductive generation of enolates from enones under hydrogenation conditions. Enolates generated in this fashion participate in catalytic C-C bond formation via carbonyl addition to aldehyde and, as demonstrated in this account, ketone partners. Notably, the use of appendant dione partners enables diastereoselective formation of cycloaldol products possessing 3-stereogenic centers, including 2-contiguous quaternary centers. |
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