Author: Amancha, Prashanth K.; Lai, Yi-Chun; Chen, I. Chia; Liu, Hsing-Jang; Zhu, Jia-Liang
Description: The Diels-Alder reactions of a variety of acyclic a-cyano a,B-unsaturated ketones have been investigated. With the assistance of boron trichloride, these compounds were found to undergo the cycloaddition readily with dienes to give the corresponding adducts in good to high yields. In addition, some could be further subjected to the reductive alkylation reactions using lithium naphthalenide (LN) and an appropriate alkylating agent, thus allowing for the generation of highly substituted cyclohexenes with the replacement of the cyano group with an alkyl substituent.
Subject headings: Diels-Alder reactions; a-Cyano a,B-unsaturated ketones; Boron trichloride; Lithium naphthalenide; Reductive alkylation
Publication year: 2010
Journal or book title: Tetrahedron
Volume: 66
Issue: 4
Pages: 871-877
Find the full text: https://www.sciencedirect.com/science/article/pii/S0040402009018365
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Serial number: 3343