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STUDIES DIRECTED TOWARD THE DESIGN OF CHIRAL ACYLATING AGENTS - THE UTILITY OF CHIRAL N-BENZOYLIMIDES IN ENANTIOSELECTIVE ALCOHOL ACYLATION

EVANS, DA; ANDERSON, JC; TAYLOR, MK; (1993) STUDIES DIRECTED TOWARD THE DESIGN OF CHIRAL ACYLATING AGENTS - THE UTILITY OF CHIRAL N-BENZOYLIMIDES IN ENANTIOSELECTIVE ALCOHOL ACYLATION. TETRAHEDRON LETT , 34 (35) 5563 - 5566.

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Abstract

N-benzoyl-4(S)-tert-butyl-2-oxazolidinone (1b) is found to be an efficient enantioselective acylating agent for aryl n-alkyl carbinols. Selective benzoylation of racemic aryl n-alkyl carbinols with kinetic selectivities of 20-30:1 for the (R) enantiomer is observed. The acylation process is promoted by formation of the derived magnesium alkoxides which may be accessed either from alcohol deprotonation with MeMgBr or through deprotonation with the Lewis acid-base combination of MgBr2/R3N.

Type:Article
Title:STUDIES DIRECTED TOWARD THE DESIGN OF CHIRAL ACYLATING AGENTS - THE UTILITY OF CHIRAL N-BENZOYLIMIDES IN ENANTIOSELECTIVE ALCOHOL ACYLATION
Keywords:ORGANIC-SOLVENTS, ENZYMES, HYDROXYL
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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