Issue 22, 2020

Rh-Catalyzed diastereo- and linear-selective α-allylation of chiral cycloenamines

Abstract

In this paper, a Rh-catalyzed diastereoselective α-allylation of cycloenamines is demonstrated. During the reaction, commercially available Wilkinson's catalyst was employed, and a chiral sulfinamide group acted as the chiral directing group. Following such a synthetic method, unusual linear substituted products were achieved, instead of branched substituted products which were most reported previously. The reaction exhibits a good chemical yield and excellent diastereoselectivity. A possible reaction mechanism was proposed. The method should be conducive to synthesizing natural products and novel drug molecules.

Graphical abstract: Rh-Catalyzed diastereo- and linear-selective α-allylation of chiral cycloenamines

Supplementary files

Article information

Article type
Research Article
Submitted
08 Sep 2020
Accepted
18 Oct 2020
First published
19 Oct 2020

Org. Chem. Front., 2020,7, 3715-3719

Rh-Catalyzed diastereo- and linear-selective α-allylation of chiral cycloenamines

X. Wang, Y. Luo, S. Qin, Y. Sun, N. Wang, J. Yan and G. Yang, Org. Chem. Front., 2020, 7, 3715 DOI: 10.1039/D0QO01087A

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