Catalytic Asymmetric [3 + 2] Annulation via Indolyl Copper-Allenylidene Intermediates: Diastereo- and Enantioselective Assembly of Pyrrolo[1,2- a]indoles

Jian Zhang; Tao Ni; Wu-Lin Yang; Wei-Ping Deng

doi:10.1021/acs.orglett.0c01594

Catalytic Asymmetric [3 + 2] Annulation via Indolyl Copper-Allenylidene Intermediates: Diastereo- and Enantioselective Assembly of Pyrrolo[1,2- a]indoles

Org Lett. 2020 Jun 5;22(11):4547-4552. doi: 10.1021/acs.orglett.0c01594. Epub 2020 May 26.

Authors

Jian Zhang¹, Tao Ni¹, Wu-Lin Yang¹, Wei-Ping Deng^{1

2}

Affiliations

¹ School of Pharmacy and Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
² Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, Jinhua 321004, China.

PMID: 32453576
DOI: 10.1021/acs.orglett.0c01594

Abstract

A catalytic asymmetric decarboxylative [3 + 2] annulation via indolyl copper-allenylidene amphiphilic intermediates has been developed. This protocol offers a straightforward method for the synthesis of biologically important pyrrolo[1,2-a]indoles bearing contiguous quaternary and tertiary stereogenic centers with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). In addition, the diversity-oriented synthesis of pyrrolo[1,2-a]indoles was achieved via versatile transformations of the alkyne-containing cycloadducts.

Publication types

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