Experimental evidence for chair-like transition states in aldol reactions of methyl ketone lithium enolates: stereoselective synthesis and utilization of a deuterium-labeled enolate as a probe of reaction stereochemistry |
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Authors: | Liu Christopher M Smith William J Gustin Darin J Roush William R |
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Institution: | Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA. |
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Abstract: | Aldol reactions of methyl ketone lithium enolates proceed via chairlike Zimmerman-Traxler transition states with 7:1 to 50:1 preference over alternative, boatlike transition structures, as determined by studies involving the configurationally stable deuterium-labeled enol silane 18 as the lithium enolate precursor. |
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