Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives

Qiang Wei; Ya-Yi Wang; Yu-Liu Du; Liu-Zhu Gong

doi:10.3762/bjoc.9.177

Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives

Beilstein J Org Chem. 2013 Aug 1:9:1559-64. doi: 10.3762/bjoc.9.177. eCollection 2013.

Authors

Qiang Wei¹, Ya-Yi Wang, Yu-Liu Du, Liu-Zhu Gong

Affiliation

¹ Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.

Abstract

A chiral phosphoric acid-catalyzed selenofunctionalization of tryptamine derivatives provides access to 3a-(phenylselenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole derivatives in high yields and with synthetically useful levels of enantioselectivity (up to 89% ee).

Keywords: catalysis; chiral phosphoric acid; hexahydropyrrolo[2,3-b]indole; indole alkaloids; natural products; selenofunctionalization.