Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 24, Pages 9330-9339Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0352934
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Metalated O-silyl cyanohydrins of beta-silyl-alpha, beta-epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving base-promoted ring opening of the epoxide, Brook rearrangement, and alkylation of the resulting allylic anion. On the basis of mechanistic studies involving competitive experiments using the diastereomeric eyanohydrins, we propose a reaction pathway involving a silicate intermediate 36 formed by a concerted process via an anti-opening of the epoxide followed by the formation of an O-Si bond.
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