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

Aram Lim; Jung Hoon Choi; Jinsung Tae

doi:10.1016/j.tetlet.2008.06.004

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

Aram Lim, Jung Hoon Choi, Jinsung Tae

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

24 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 language	English
Pages (from-to)	4882-4885
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2008.06.004
Publication status	Published - 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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10.1016/j.tetlet.2008.06.004

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title = "Organocatalytic α-amination-allylation-RCM strategy: enantioselective synthesis of cyclic hydrazines",

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.",

author = "Aram Lim and Choi, {Jung Hoon} and Jinsung Tae",

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. ",

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doi = "10.1016/j.tetlet.2008.06.004",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Organocatalytic α-amination-allylation-RCM strategy

T2 - enantioselective synthesis of cyclic hydrazines

AU - Lim, Aram

AU - Choi, Jung Hoon

AU - Tae, Jinsung

N1 - 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.

PY - 2008/8/11

Y1 - 2008/8/11

N2 - 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.

AB - 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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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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