Download PDF
Synlett 1993; 1993(5): 359-361
DOI: 10.1055/s-1993-22456
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Organocerium Additions to Chiral α,α-Dialkoxy Hydrazones: Asymmetric Synthesis of N-Protected α-Amino Acetals and α-Amino Aldehydes

Scott E. Denmark* , Olivier Nicaise
  • *Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA
Further Information

Publication History

Publication Date:
19 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

A general and selective procedure for the diastereoselective additions of organocerium reagents to chiral α,α-dialkoxy hydrazones has been developed. The best reagent combination involved a 6:1 composition of RMet to CeCl3. Excellent yields and high selectivities were obtained after trapping as the iso-butyl carbamates. Lithiumammonia cleavage of the N-N bond followed by hydrolysis with TMSI afforded the protected α-amino aldehydes.

      >