What question did this study set out to answer?

This research investigates how methyl cyanoformate acylates enolates and the selectivity involved.

January 1, 1990

C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity

SCSimon R. CrabtreeAustralian National University WCWen‐Dao ChuChina West Normal University LMLewis N. ManderAustralian National University

Key Points

This research investigates how methyl cyanoformate acylates enolates and the selectivity involved.
Explored acylation of preformed lithium enolates using methyl cyanoformate.
Analyzed the influence of diethyl ether as a solvent on product outcomes.
Assessed diastereofacial selectivity in reactions involving chiral enolates.
C-acylation products increased in sterically hindered substrates with diethyl ether solvent.
Diastereofacial selectivity in chiral enolates mirrors that seen in C-alkylations in most cases.
In some instances, higher steric demand of cyanoformate led to exceptions in selectivity.

Abstract

The scope and limitations of the acylation of preformed lithium enolates by methyl cyanoformate have been explored further. In particular, the proportion of C-acylation products in sterically hindered substrates is significantly enhanced by the use of diethyl ether as solvent, while diastereofacial selectivity in the reactions of chiral enolates is found to be similar to that observed for C-alkylations in most cases. Exceptions may occur as a consequence of the higher steric demand of the cyanoformate reagent, however.

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