N- Heterocyclic carbene catalyzed C-acylation reaction for access to linear aminoenones

An N -heterocyclic carbene (NHC)-catalyzed carbonyl nucleophilic substitution reaction between 1cyclopropylcarbaldehydes and N- sulfonyl imines is developed for access to linear fi-aminoenone products. The fi-aminoenones containing cyclopropyl fragments can be afforded in moderate to excellent yields under mild conditions. The reaction features excellent trans -diastereoselectivities and the desired aminoenone products are all afforded as Z -isomers.(c) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

A N-heterocyclic carbene (NHC)-catalyzed carbonyl nucleophilic substitution reaction between 1-cyclopropylcarbaldehydes and N-sulfonyl imines is developed for the synthesis of linear fi-aminoenone products. The reaction proceeds under mild conditions and provides the desired fi-aminoenones containing cyclopropyl fragments in moderate to excellent yields. The products exhibit excellent trans-diastereoselectivities and all exist as Z-isomers.