Organocerium additions to chiral α,α-dialkoxy hydrazones: Asymmetric synthesis of JV-protected a-amino acetals and α-amino aldehydes

Scott E. Denmark, Olivier Nicaise

Research output: Contribution to journalArticlepeer-review

Abstract

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 uo-butyl carbamates. Lithium-ammonia cleavage of the N-N bond followed by hydrolysis with TMSI afforded the protected ot-amino aldehydes.

Original languageEnglish (US)
Pages (from-to)359-361
Number of pages3
JournalSynlett
Volume1993
Issue number5
DOIs
StatePublished - May 1993

ASJC Scopus subject areas

  • Organic Chemistry

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