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Reductive Cyclization of Bromoenynamides with Alcohols as Hydride Source: Synthesis and Reactions of 2-Amidodienes

Abstract:

Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium-catalyzed cyclization to cyclic 2-amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5-8), and the nature of the alcohol and base. Reaction of the dienes with a range of dienophiles (including alkenes, al...

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Publication status:
Published

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Publisher copy:
10.1002/adsc.201200703

Authors


Greenaway, RL More by this author
Campbell, CD More by this author
Chapman, HA More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
ADVANCED SYNTHESIS and CATALYSIS
Volume:
354
Issue:
17
Pages:
3187-3194
Publication date:
2012-11-05
DOI:
EISSN:
1615-4169
ISSN:
1615-4150
URN:
uuid:d2a827a0-5a17-45d9-83b7-3e20471ffb35
Source identifiers:
366806
Local pid:
pubs:366806

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