期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 5, 页码 2753-2762出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b03205
关键词
-
资金
- NSF [0515715, CHE 1464494]
- Division Of Chemistry [1464494] Funding Source: National Science Foundation
Alkylations of acyclic, lithiated 4-alkoxyalk-4-enenitriles are highly diastereoselective with an unusual electrophile-dependent preference. Alkyl halides, sulfur, chlorine, and acyl cyanide electrophiles intercept a series of lithiated 4-alkoxyalk-4-enenitriles to install contiguous tertiary-quaternary stereocenters with high diastereoselectivity, whereas acylations with ester and carbonate electrophiles are modestly selective. The diastereoselectivity is consistent with electrophilic attack on the most accessible face of the lithated nitrile for most electrophiles except ester and carbonate electrophiles, which likely precoordinate the lithiated nitrile before acylation. Intercepting the lithiated 4-alkoxyalk-4-enenitriles with a range of electrophiles provide insight into the criteria for otherwise challenging diastereoselective alkylations and acylations of acyclic nitriles.
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