Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers: synthesis of alkylidenecyclobutenones and their reactivity in ring-opening and ring expansion

Ling Chen; Jian Cao; Zheng Xu; Zhan-Jiang Zheng; Yu-Ming Cui; Li-Wen Xu

doi:10.1039/C6CC04648G

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Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers: synthesis of alkylidenecyclobutenones and their reactivity in ring-opening and ring expansion†

Ling Chen,^a Jian Cao,*^a Zheng Xu,^a Zhan-Jiang Zheng,^a Yu-Ming Cui^a and Li-Wen Xu*^ab

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* Corresponding authors

^a Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou 311121, P. R. China
E-mail: caojian@hznu.edu.cn, liwenxu@hznu.edu.cn

^b State Key Laboratory for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences (CAS), P. R. China

Abstract

A family of four-membered enones, polysubstituted alkylidenecyclobutenones, were easily prepared by a Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers. This challenging regioselective [2+2] cycloaddition enables the efficient construction and conversion of four-membered enones, which provides high-value and structurally diverse products through the unexpected ring-opening and ring expansion of alkylidenecyclobutenone with Grignard reagents, organolithium, primary amines, and water.

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DOI: https://doi.org/10.1039/C6CC04648G
Article type: Communication
Submitted: 03 Jun 2016
Accepted: 03 Jul 2016
First published: 08 Jul 2016

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Chem. Commun., 2016,52, 9574-9577

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Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers: synthesis of alkylidenecyclobutenones and their reactivity in ring-opening and ring expansion

L. Chen, J. Cao, Z. Xu, Z. Zheng, Y. Cui and L. Xu, Chem. Commun., 2016, 52, 9574 DOI: 10.1039/C6CC04648G

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Chemical Communications

Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers: synthesis of alkylidenecyclobutenones and their reactivity in ring-opening and ring expansion†

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Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers: synthesis of alkylidenecyclobutenones and their reactivity in ring-opening and ring expansion

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