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

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

Org Biomol Chem. 2021 Mar 4;19(8):1727-1731. doi: 10.1039/d0ob02508a.

Authors

Xing Guo¹, Xuling Chen², Yuyu Cheng², Xiaoyong Chang², Xuechen Li³, Pengfei Li²

Affiliations

¹ 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. [email protected] [email protected] and Department of Chemistry, State Key Lab of Synthetic Chemistry, The University of Hong Kong, Hong Kong, China. [email protected].
² 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. [email protected] [email protected].
³ Department of Chemistry, State Key Lab of Synthetic Chemistry, The University of Hong Kong, Hong Kong, China. [email protected].

PMID: 33538742
DOI: 10.1039/d0ob02508a

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.

Publication types

Research Support, Non-U.S. Gov't