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Issue 7, 2002
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A unique rhodium-catalyzed rearrangement process: isomerization of an alkyne to a 1,3-diene with concomitant migration of a formyl group. An expeditious route to dienals from readily available 4-alkynals

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Abstract

In CH2Cl2, [Rh(BINAP)]BF4 catalyzes the isomerization of 4-alkynals to dienals with excellent regio- and stereoselectivity; this new process compares favorably with previously reported methods for the synthesis of this class of compounds; a possible pathway for this unusual rearrangement is provided.

Graphical abstract: A unique rhodium-catalyzed rearrangement process: isomerization of an alkyne to a 1,3-diene with concomitant migration of a formyl group. An expeditious route to dienals from readily available 4-alkynals

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Article information


Submitted
03 Jan 2002
Accepted
06 Feb 2002
First published
04 Mar 2002

Chem. Commun., 2002, 684-685
Article type
Communication

A unique rhodium-catalyzed rearrangement process: isomerization of an alkyne to a 1,3-diene with concomitant migration of a formyl group. An expeditious route to dienals from readily available 4-alkynals

K. Tanaka and G. C. Fu, Chem. Commun., 2002, 684
DOI: 10.1039/B200208F

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