Issue 88, 2018

Catalytic enantioselective ene-type reactions of vinylogous hydrazone: construction of α-methylene-γ-butyrolactone derivatives

Abstract

The catalytic asymmetric ene-type reactions of vinylogous hydrazone were accomplished by using chiral N,N′-dioxide–metal salt complexes as catalysts. A wide range of electrophiles, including isatins, α-ketoester, imines, and aldehydes reacted with (E)-2-methyl-N-(piperidin-1-yl)prop-2-en-1-imine efficiently, affording the corresponding homoallylic alcohols and amines in high yields (up to 99%) with excellent ee values (up to 99%). The methodology provided a convenient way to synthesize bioactive chiral α-methylene-γ-butyrolactone derivatives.

Graphical abstract: Catalytic enantioselective ene-type reactions of vinylogous hydrazone: construction of α-methylene-γ-butyrolactone derivatives

Supplementary files

Article information

Article type
Communication
Submitted
18 Sep 2018
Accepted
12 Oct 2018
First published
13 Oct 2018

Chem. Commun., 2018,54, 12511-12514

Catalytic enantioselective ene-type reactions of vinylogous hydrazone: construction of α-methylene-γ-butyrolactone derivatives

H. Zhang, Q. Yao, W. Cao, S. Ge, J. Xu, X. Liu and X. Feng, Chem. Commun., 2018, 54, 12511 DOI: 10.1039/C8CC07567K

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