Journal
ACCOUNTS OF CHEMICAL RESEARCH
Volume 36, Issue 9, Pages 701-712Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ar020133k
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Allenes with a nucleophilic functionality connected to the alpha-carbon atom have been shown to be versatile building blocks for the synthesis of gamma-butenolides, gamma-lactams, gamma-iminolactones, vinylic epoxides, 4-amino-2-alkenols, 2-amino-3-alkenols, 2,5-dihydrofurans, furans, vinylic cyclopropanes, and cyclopentenes, depending on the nature of the nucleophilic centers. The reaction may proceed via the carbometalation-nucleophilic attack mechanism or nucleometallation-reductive elimination. The stereochemical outcomes by these two pathways are different.
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