Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 66, Issue 26, Pages 8779-8786Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0104328
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A remarkable effect of (C6F5O)(3)Al for promoting the rearrangement of epoxy acylates via stable cation intermediates was found, and new methods for constructing chiral benzylic, vinylic, and acetylenic quaternary carbon centers were developed. During the study, the importance of the ionic nature of the O-metal bond in the intermediates of such epoxides was addressed. This method was applied to the asymmetric total synthesis of (S)-(+)-sporochnol A.
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