☆ 4.8 Article

Explaining the Disparate Stereoselectivities of N-Oxide Catalyzed Allylations and Propargylations of Aldehydes

ORGANIC LETTERS (2012)

期刊

ORGANIC LETTERS

卷 14, 期 20, 页码 5310-5313

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol302493d

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Chemistry, Organic

资金

Welch Foundation [A-1775]

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Reagent

摘要

A simple electrostatic model explains the enhanced stereoselectivity of N-oxide catalyzed allylations compared to propargylations, which in turn explicates the dearth of stereoselective N-oxide propargylation catalysts. These results suggest that N-oxide catalysts that are effective for both allylations and propargylations can be designed by targeting inherently stereoselective ligand configurations and through the manipulation of distortion effects in the operative transition states.

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