All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization.

Yanli Yin, Yunqiang Li, Theo Goncalves, Qiangqiang Zhan, Guanghui Wang, Xiaowei Zhao, Baokun Qiao, Kuo-Wei Huang, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes is reported. Under cooperative photoredox and chiral Brønsted acid catalysis, cyclopropylamines with α-branched 2-vinylazaarenes can undergo a sequential two-step radical process, furnishing various valuable chiral azaarene-substituted cyclopentanes. The use of the rigid and confined C2-symmetric imidodiphosphoric acid catalysts achieves high enantio- and diastereo-selectivities for these asymmetric [3 + 2] cycloadditions.
Original languageEnglish (US)
JournalJournal of the American Chemical Society
DOIs
StatePublished - Nov 5 2020

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