Volume 21, Issue 37
Preparative Organic Chemistry
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ChemInform Abstract: A Mild Four-Carbon Homologation of Aldehydes to E,E-Dienamines.

A. S. KENDE

A. S. KENDE

Dep. Chem., Univ. Rochester, Rochester, NY 14627, USA

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R. J. DEVITA

R. J. DEVITA

Dep. Chem., Univ. Rochester, Rochester, NY 14627, USA

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First published: September 11, 1990

Abstract

The protected propargylamine (III) reacts with tributylstannane (IV) to form the aminoalkenylstannane (V).

ChemInform Abstract

The protected propargylamine (III) reacts with tributylstannane (IV) to form the aminoalkenylstannane (V). This is coupled with the vinylic iodides (VIII), prepared from the aldehydes (VI) and (VII) in the presence of CrCl2, to give the dienes (IX). (IXd) is converted to the pivalamide (XI).

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