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Synlett 2001; 2001(Special Issue): 1024-1029
DOI: 10.1055/s-2001-14652
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Diastereoselective Aldol Addition Reactions of a Chiral Methyl Ketone Trichlorosilyl Enolate under Lewis Base Catalysis

Scott E. Denmark* , Shinji Fujimori
  • *Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA; Fax (217) 333-3984; E-mail: sdenmark@uiuc.edu
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Publication History

Publication Date:
31 December 2001 (online)

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The trichlorosilyl enolate of a chiral methyl ketone bearing an oxygen substituent (OTBS) on the β-position undergoes highly diastereoselective aldol addition to a variety of achiral aldehydes in good yield. The stereochemical course of the reaction is primarily controlled by the configuration of the chiral phosphoramide which serves as an effective catalyst for this transformation.

aldol addition - trichlorosilyl enolate - Lewis base catalysis - diastereoselection

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