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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 13
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Original Articles

Nickel Acetylacetonate-Induced 1,4-Additions of 1-Alkenyl(Disiamyl)Boranes to α,β-Unsaturated Ketones, Esters and Nitriles

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Pages 2503-2509 | Received 20 Oct 1995, Published online: 23 Aug 2006
 

Abstract

The conjugate addition of 1-alkenyl(disiamyl)boranes to α,β-unsaturated ketones, esters, or nitriles was carried out in the presence of Ni(acac)2 and triethylamine in DMF. The reactions provided γ,δ-unsaturated ketones, esters, and nitriles in high yields while retaining the original configuration of the 1-alkenylboranes. A similar addition reaction of 1-alkenyl(disiamyl)boranes to 1-acetyl-2-vinylcyclopropane produced the terminal and internal coupling products, 5,8-alkadien-2-on and 5-ethenyl-6-alken-2-on, in high yields in some cases with high regioselectivity favoring the terminal addition products.

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