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Issue 9, 2021
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Stereodivergent Pd/Cu catalysis: asymmetric alkylation of racemic symmetrical 1,3-diphenyl allyl acetates

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Abstract

We report a stereodivergent Pd/Cu catalyst system that was successfully applied to the asymmetric allylic alkylation of symmetrical 1,3-disubstituted allyl acetates with prochiral imino esters, providing efficient access to enantiopure products bearing vicinal stereocenters in a fully stereodivergent manner. The protocol proceeds smoothly under mild reaction conditions and can accommodate a range of imino esters, delivering the substituted products in high yields and with excellent diastereoselectivities (up to >20 : 1 dr) and enantioselectivities (up to >99% ee).

Graphical abstract: Stereodivergent Pd/Cu catalysis: asymmetric alkylation of racemic symmetrical 1,3-diphenyl allyl acetates

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Article information


Submitted
15 Dec 2020
Accepted
30 Jan 2021
First published
18 Feb 2021

Org. Biomol. Chem., 2021,19, 1955-1959
Article type
Communication

Stereodivergent Pd/Cu catalysis: asymmetric alkylation of racemic symmetrical 1,3-diphenyl allyl acetates

L. Zhao, G. Li, R. He, P. Liu, F. Wang, X. Huo, M. Zhao and W. Zhang, Org. Biomol. Chem., 2021, 19, 1955
DOI: 10.1039/D0OB02499F

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