Radical-mediated diamination of alkenes with phenylhydrazine and azodicarboxylates: Highly diastereoselective synthesis of trans-diamines from cycloalkenes

Ming Kui Zhu; Yu Chen Chen; Teck Peng Loh

doi:10.1002/chem.201203832

Radical-mediated diamination of alkenes with phenylhydrazine and azodicarboxylates: Highly diastereoselective synthesis of trans-diamines from cycloalkenes

Ming Kui Zhu, Yu Chen Chen, Teck Peng Loh^*

^*Corresponding author for this work

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

59 Citations (Scopus)

Abstract

Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc=tert-butoxycarbonyl). This process works with the assistance of acetic acid by means of a radical mechanism and displays a high trans selectivity when cycloalkene substrates were used in the reaction.

Original language	English
Pages (from-to)	5250-5254
Number of pages	5
Journal	Chemistry - A European Journal
Volume	19
Issue number	17
DOIs	https://doi.org/10.1002/chem.201203832
Publication status	Published - Apr 22 2013
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Organic Chemistry

Keywords

alkenes
cyclization
diamination
diastereoselectivity
radicals

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abstract = "Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc=tert-butoxycarbonyl). This process works with the assistance of acetic acid by means of a radical mechanism and displays a high trans selectivity when cycloalkene substrates were used in the reaction.",

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AU - Chen, Yu Chen

AU - Loh, Teck Peng

PY - 2013/4/22

Y1 - 2013/4/22

N2 - Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc=tert-butoxycarbonyl). This process works with the assistance of acetic acid by means of a radical mechanism and displays a high trans selectivity when cycloalkene substrates were used in the reaction.

AB - Metal-free synthesis: Diamination of alkenes by using phenylhydrazine and azodicarboxylates could be achieved in a one-pot manner under very mild conditions (see scheme; Boc=tert-butoxycarbonyl). This process works with the assistance of acetic acid by means of a radical mechanism and displays a high trans selectivity when cycloalkene substrates were used in the reaction.

KW - alkenes

KW - cyclization

KW - diamination

KW - diastereoselectivity

KW - radicals

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ER -

Radical-mediated diamination of alkenes with phenylhydrazine and azodicarboxylates: Highly diastereoselective synthesis of trans-diamines from cycloalkenes

Abstract

ASJC Scopus Subject Areas

Keywords

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