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

Aram Lim, Jung Hoon Choi, Jinsung Tae

Research output: Contribution to journalArticle

21 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

Fingerprint

Hydrazines
Allylation
Amination
Aldehydes
Indium
Enantioselectivity
Proline

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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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.",
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Organocatalytic α-amination-allylation-RCM strategy : enantioselective synthesis of cyclic hydrazines. / Lim, Aram; Choi, Jung Hoon; Tae, Jinsung.

In: Tetrahedron Letters, Vol. 49, No. 33, 11.08.2008, p. 4882-4885.

Research output: Contribution to journalArticle

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