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Paper | Special issue | Vol 70, No. 1, 2006, pp.185-199
Published online, 20th June, 2006
DOI: 10.3987/COM-06-S(W)3
Strecker Reactions of Chiral N-Acylhydrazones

Hui Ding and Gregory K. Friestad*

*415 Chemistry Building, Department of Chemistry, University of Iowa, 320 North Madison Street, Iowa City, Iowa 52242, U.S.A.

Abstract

Development of a method for addition of trimethylsilyl cyanide to chiral oxazolidinone-derived N-acylhydrazones is described. The diastereoselectivity was found to be highly dependent on the substituent of the oxazolidinone moiety; 4-phenyl-2-oxazolidinone achieved much higher stereocontrol than four other oxazolidinones screened. The reaction gives modest selectivity with aliphatic hydrazones and excellent selectivity with hydrazones prepared from aromatic aldehydes.