Issue 74, 2018

Asymmetric synthesis of polysubstituted methylenecyclobutanes via catalytic [2+2] cycloaddition reactions of N-allenamides

Abstract

A highly enantioselective [2+2] cycloaddition reaction of alkylidene malonates with the internal C[double bond, length as m-dash]C bond of N-allenamides was developed with a MgII/N,N′-dioxide complex as a catalyst. Various polysubstituted methylenecyclobutanes were afforded in good yields (up to 99%) and excellent enantioselectivities (up to 96% ee) under mild conditions. The utility of the donor–acceptor cyclobutane product was demonstrated as a masked 1,4-dipole in the formal [4+2] annulation reaction with a silyl enol ether.

Graphical abstract: Asymmetric synthesis of polysubstituted methylenecyclobutanes via catalytic [2+2] cycloaddition reactions of N-allenamides

Supplementary files

Article information

Article type
Communication
Submitted
07 Aug. 2018
Accepted
23 Aug. 2018
First published
23 Aug. 2018

Chem. Commun., 2018,54, 10511-10514

Asymmetric synthesis of polysubstituted methylenecyclobutanes via catalytic [2+2] cycloaddition reactions of N-allenamides

X. Zhong, Q. Tang, P. Zhou, Z. Zhong, S. Dong, X. Liu and X. Feng, Chem. Commun., 2018, 54, 10511 DOI: 10.1039/C8CC06416D

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