Issue 8, 2022

Access to axially chiral aryl 1,3-dienes by transient group directed asymmetric C–H alkenylations

Abstract

We present a Pd-catalyzed atroposelective preparation of aryl 1,3-dienes from readily available styrenes and olefins through an aldehyde derived transient chiral auxiliary, proceeding by enantioselective olefinic C–H alkenylation of styrenes via seven-membered endo-cyclometallation. The generality of the protocol has been demonstrated by the smooth conversion of a wide range of 2-vinyl benzaldehyde derivatives to afford up to 99% yields and high to excellent enantioselectivities (up to >99% ee). The derived axially chiral carboxylic acid was demonstrated to be a more efficient ligand in the Cp*Co(III)-catalyzed asymmetric C(sp3)–H alkylation.

Graphical abstract: Access to axially chiral aryl 1,3-dienes by transient group directed asymmetric C–H alkenylations

Supplementary files

Article information

Article type
Research Article
Submitted
08 feb 2022
Accepted
24 feb 2022
First published
25 feb 2022

Org. Chem. Front., 2022,9, 2109-2115

Access to axially chiral aryl 1,3-dienes by transient group directed asymmetric C–H alkenylations

C. Shen, Y. Zhu, W. Shen, S. Jin, G. Zhong, S. Luo, L. Xu, L. Zhong and J. Zhang, Org. Chem. Front., 2022, 9, 2109 DOI: 10.1039/D2QO00161F

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