Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines via Palladium-Catalyzed Addition of Arylboronic Acids

Yang Zhao; Xiao-Qing Wang; Yan-Jiang Yu; Yong-Gui Zhou

doi:10.1021/acs.joc.0c02509

Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines via Palladium-Catalyzed Addition of Arylboronic Acids

J Org Chem. 2021 Jan 1;86(1):1262-1272. doi: 10.1021/acs.joc.0c02509. Epub 2020 Dec 18.

Authors

Yang Zhao^{1

2}, Xiao-Qing Wang¹, Yan-Jiang Yu¹, Yong-Gui Zhou^{1

3}

Affiliations

¹ State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, People's Republic of China.
² University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People's Republic of China.

PMID: 33337149
DOI: 10.1021/acs.joc.0c02509

Abstract

A facile method for kinetic resolution of [2.2]paracyclophane-derived cyclic N-sulfonylimines based on palladium-catalyzed addition of arylboronic acids was developed, giving two kinds of planar chiral [2.2]paracyclophane derivatives in excellent diastereoselectivities and up to 99% of enantioselectivities with high selectivity factors (s up to 128).