Enantioselective Rhodium-Catalyzed Hydrogenation of (Z)- N-Sulfonyl-α-dehydroamido Boronic Esters

Zhenya Li; Ronghua Xu; Huichuang Guo; He Yang; Guangqing Xu; Enxue Shi; Junhua Xiao; Wenjun Tang

doi:10.1021/acs.orglett.1c04157

Enantioselective Rhodium-Catalyzed Hydrogenation of (Z)- N-Sulfonyl-α-dehydroamido Boronic Esters

Org Lett. 2022 Jan 21;24(2):714-719. doi: 10.1021/acs.orglett.1c04157. Epub 2022 Jan 3.

Authors

Zhenya Li¹, Ronghua Xu², Huichuang Guo¹, He Yang², Guangqing Xu², Enxue Shi¹, Junhua Xiao¹, Wenjun Tang^{2

3}

Affiliations

¹ State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China.
² State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032, China.
³ School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou 310024, China.

PMID: 34978454
DOI: 10.1021/acs.orglett.1c04157

Abstract

Highly enantioselective rhodium-catalyzed hydrogenation of (Z)-N-sulfonyl-α-dehydroamido boronic esters is realized for the first time using a JosiPhos-type ligand. This method has enabled convenient synthesis of a series of enantio-enriched N-sulfonyl-α-amido boronic esters in good yields and excellent enantioselectivities (up to 99% ee).