Phosphine-Catalyzed Atroposelective Formal [3 + 2] Cycloaddition Desymmetrization of N-Arylmaleimides

Huamin Wang; Yibo Wei; Yuqiang Li; Shuangshuang Long; Li-Juan Sun; Shixiong Li; Ying-Wu Lin

doi:10.1021/acs.orglett.2c02208

Phosphine-Catalyzed Atroposelective Formal [3 + 2] Cycloaddition Desymmetrization of N-Arylmaleimides

Org Lett. 2022 Sep 16;24(36):6494-6498. doi: 10.1021/acs.orglett.2c02208. Epub 2022 Sep 7.

Authors

Huamin Wang¹, Yibo Wei¹, Yuqiang Li², Shuangshuang Long¹, Li-Juan Sun³, Shixiong Li¹, Ying-Wu Lin^{1

3

4}

Affiliations

¹ School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001, People's Republic of China.
² College of Chemistry and Chemical Engineering, Central South University, Changsha, Hunan 410083, People's Republic of China.
³ Hengyang Medical College, University of South China, Hengyang, Hunan 421001, People's Republic of China.
⁴ Laboratory of Protein Structure and Function, University of South China Medical School, Hengyang, Hunan 421001, People's Republic of China.

PMID: 36069471
DOI: 10.1021/acs.orglett.2c02208

Abstract

Herein, a new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was devised by [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This desymmetrization process allows for quick construction of both two stereogenic carbon centers and a remote C_Ar-N atropisomeric chirality. A series of structurally diverse N-aryl succinimides were obtained with good to excellent yields, diastereoselectivities, and enantioselectivities. The process is mild, efficient, and scalable and features a broad substrate scope.