Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

Hao-Peng Lv; Xiao-Peng Yang; Bai-Lin Wang; Hao-Di Yang; Xing-Wang Wang; Zheng Wang

doi:10.1021/acs.orglett.1c01411

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

Org Lett. 2021 Jun 18;23(12):4715-4720. doi: 10.1021/acs.orglett.1c01411. Epub 2021 Jun 7.

Authors

Hao-Peng Lv¹, Xiao-Peng Yang¹, Bai-Lin Wang¹, Hao-Di Yang¹, Xing-Wang Wang¹, Zheng Wang²

Affiliations

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou, 215123, China.
² State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 34096732
DOI: 10.1021/acs.orglett.1c01411

Abstract

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).