Iridium-Catalyzed Enantioselective Synthesis of Pyrrole-Annulated Medium-Sized-Ring Compounds

Lin Huang; Yue Cai; Chao Zheng; Li-Xin Dai; Shu-Li You

doi:10.1002/anie.201705068

Iridium-Catalyzed Enantioselective Synthesis of Pyrrole-Annulated Medium-Sized-Ring Compounds

Angew Chem Int Ed Engl. 2017 Aug 21;56(35):10545-10548. doi: 10.1002/anie.201705068. Epub 2017 Jul 19.

Authors

Lin Huang¹, Yue Cai¹, Chao Zheng¹, Li-Xin Dai¹, Shu-Li You^{1

2}

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
² Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China.

PMID: 28665043
DOI: 10.1002/anie.201705068

Abstract

Enantioselective synthesis of pyrrole-annulated medium-sized-ring compounds by an iridium-catalyzed allylic dearomatization/retro-Mannich/hydrolysis sequence is presented. Various substituted pyrrole-annulated seven- and eight-membered-ring products were obtained under mild reaction conditions with moderate to good yields and excellent enantioselectivity. Additionally, these products contain a scaffold widely distributed in natural products and biologically active compounds. The current method provides a convenient way for accessing such pyrrole-anuulated medium-sized-ring compounds.

Keywords: annulations; asymmetric catalysis; heterocycles; iridium; medium-sized rings.

Publication types

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