Organocatalytic α-amination-allylation-RCM strategy: enantioselective synthesis of cyclic hydrazines

Aram Lim, Jung Hoon Choi, Jinsung Tae

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22 Citations (Scopus)

Abstract

A highly enantioselective method for the synthesis of cyclic hydrazines by using organocatalytic α-amination-allylation-RCM strategy is described. Proline-catalyzed α-amination of aldehydes followed by indium-mediated one-pot allylation of the crude α-hydrazino aldehydes produces 1,2-aminoalcohols in high enantio- and diastereoselectivities. The 1,2-aminoalcohols are further converted into cyclic hydrazines by using ring-closing metathesis (RCM) reaction.

Original languageEnglish
Pages (from-to)4882-4885
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number33
DOIs
Publication statusPublished - 2008 Aug 11

Bibliographical note

Funding Information:
This work was supported by the Center for Bioactive Molecular Hybrids (MOST/KOSEF). A.L. thanks BK 21 program (KRF). J.T. thanks Yonsei University and Professor K.W.J. at USC for the supports during the sabbatical year.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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