Organocatalytic enantioselective [2 + 4]-annulation of γ-substituted allenoates with N-acyldiazenes for the synthesis of optically active 1,3,4-oxadiazines

Xing Guo; Xuling Chen; Yuyu Cheng; Xiaoyong Chang; Xuechen Li; Pengfei Li

doi:10.1039/D0OB02508A

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Organocatalytic enantioselective [2 + 4]-annulation of γ-substituted allenoates with N-acyldiazenes for the synthesis of optically active 1,3,4-oxadiazines†

Xing Guo,^ab Xuling Chen,^a Yuyu Cheng,^a Xiaoyong Chang,^a Xuechen Li

*^b and Pengfei Li

*^a

Author affiliations

* Corresponding authors

^a Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology, Shenzhen 518055, China
E-mail: lipf@sustech.edu.cn, flyli1980@gmail.com

^b Department of Chemistry, State Key Lab of Synthetic Chemistry, The University of Hong Kong, Hong Kong, China
E-mail: xuechenl@hku.hk

Abstract

An enantioselective [2 + 4]-annulation of γ-substituted allenoates with N-acyldiazenes has been developed for the first time. In the presence of an L-proline-derived DMAP analogue, the annulation proceeded smoothly to afford a broad range of 1,3,4-oxadiazine derivatives in good to excellent yields with high stereoselectivities.

This article is part of the themed collections: Synthetic methodology in OBC and Catalysis & biocatalysis in OBC

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DOI: https://doi.org/10.1039/D0OB02508A
Article type: Communication
Submitted: 16 Dec 2020
Accepted: 26 Jan 2021
First published: 26 Jan 2021

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Org. Biomol. Chem., 2021,19, 1727-1731

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Organocatalytic enantioselective [2 + 4]-annulation of γ-substituted allenoates with N-acyldiazenes for the synthesis of optically active 1,3,4-oxadiazines

X. Guo, X. Chen, Y. Cheng, X. Chang, X. Li and P. Li, Org. Biomol. Chem., 2021, 19, 1727 DOI: 10.1039/D0OB02508A

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Organic & Biomolecular Chemistry

Organocatalytic enantioselective [2 + 4]-annulation of γ-substituted allenoates with N-acyldiazenes for the synthesis of optically active 1,3,4-oxadiazines†

Abstract

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Organocatalytic enantioselective [2 + 4]-annulation of γ-substituted allenoates with N-acyldiazenes for the synthesis of optically active 1,3,4-oxadiazines

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