Copper(I)-Catalyzed Kinetic Resolution of N-Sulfonylaziridines with Indoles: Efficient Construction of Pyrroloindolines

Zhuo Chai; You-Min Zhu; Pei-Jun Yang; Shaoyin Wang; Shaowu Wang; Zhen Liu; Gaosheng Yang

doi:10.1021/jacs.5b05820

Copper(I)-Catalyzed Kinetic Resolution of N-Sulfonylaziridines with Indoles: Efficient Construction of Pyrroloindolines

J Am Chem Soc. 2015 Aug 19;137(32):10088-91. doi: 10.1021/jacs.5b05820. Epub 2015 Aug 4.

Authors

Zhuo Chai¹, You-Min Zhu¹, Pei-Jun Yang¹, Shaoyin Wang¹, Shaowu Wang^{1

2}, Zhen Liu¹, Gaosheng Yang¹

Affiliations

¹ †Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.
² ‡State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China.

PMID: 26204063
DOI: 10.1021/jacs.5b05820

Abstract

The first Lewis acid catalyzed [3 + 2] annulation of indoles and 2-aryl-N-tosylaziridines was realized by using copper(I)/chiral diphosphine complexes as a catalyst. With this method, a variety of uniquely substituted chiral pyrroloindolines bearing multiple contiguous stereogenic centers were facilely accessed in a straightforward, high-yielding, and highly stereoselective way under mild conditions.