Journal
ORGANIC LETTERS
Volume 11, Issue 1, Pages 177-180Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802280c
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- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Kurata Foundation
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Palladium-catalyzed reactions of various 2-bromo-3-exo-methylenecycloalkenes with a stabilized nucleophile were examined. When the carbocycles were nine-membered or larger, the corresponding endocyclic allenes were Isolated in excellent yields. In a reaction of the eight-membered cyclic substrate, initial formation of a cycloocta-1,2-diene derivative was detected; however, it dimerized slowly. The seven-membered carbocycle was Inert to the reaction, Using a chiral Pd-catalyst, an axially chiral endocyclic allene was obtained In 65% ee. The cyclic allenes were applied to [2 + 2]cycloaddition with ketenes, and the stereoselectivity was studied.
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