Catalytic asymmetric Pictet-Spengler-type reaction for the synthesis of optically active indolo[3,4-cd][1]benzazepines

Dao-Juan Cheng; Hai-Bian Wu; Shi-Kai Tian

doi:10.1021/ol202361t

Catalytic asymmetric Pictet-Spengler-type reaction for the synthesis of optically active indolo[3,4-cd][1]benzazepines

Org Lett. 2011 Oct 21;13(20):5636-9. doi: 10.1021/ol202361t. Epub 2011 Sep 26.

Authors

Dao-Juan Cheng¹, Hai-Bian Wu, Shi-Kai Tian

Affiliation

¹ Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.

PMID: 21942575
DOI: 10.1021/ol202361t

Abstract

A new strategy has been introduced to develop a catalytic asymmetric Pictet-Spengler-type reaction by replacing the aldehyde with an imine. A range of 4-(2-aminoaryl)indoles smoothly undergo the chiral phosphoric acid catalyzed asymmetric Pictet-Spengler-type reaction with imines at room temperature to give structurally diverse indolo[3,4-cd][1]benzazepines in good to excellent yields and ee.