Issue 1, 2022

A combined experimental and computational study of NHC-catalyzed allylation of allenoate with MBH esters: new regiospecific and stereoselective access to 1,5-enyne

Abstract

An NHC-catalyzed regiospecific allylation of α-substituted allenoates with MBH carbonates derived from aryl aldehyde furnished highly functionalized 1,5-enynes bearing a quaternary carbon successfully. Combining with DFT calculations, the reaction mechanism of this conversion was proposed. This method has the advantages of high regioselectivity, good yields and mild reaction conditions. This transformation not only provided a new access to 1,5-enyne, but also enriched the chemistry of allenoates and NHC catalysis.

Graphical abstract: A combined experimental and computational study of NHC-catalyzed allylation of allenoate with MBH esters: new regiospecific and stereoselective access to 1,5-enyne

Supplementary files

Article information

Article type
Research Article
Submitted
23 Jul 2021
Accepted
09 Nov 2021
First published
09 Nov 2021

Org. Chem. Front., 2022,9, 51-57

A combined experimental and computational study of NHC-catalyzed allylation of allenoate with MBH esters: new regiospecific and stereoselective access to 1,5-enyne

F. Sun, F. Lu, X. Song, W. Wu, K. Zhang, C. Yu, T. Li, D. Wei and C. Yao, Org. Chem. Front., 2022, 9, 51 DOI: 10.1039/D1QO01083B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements