Enantioselective rhodium-catalyzed arylation of cyclic N-sulfamidate alkylketimines: a new access to chiral β-alkyl-β-aryl amino alcohols

Ya-Jing Chen; Ya-Heng Chen; Chen-Guo Feng; Guo-Qiang Lin

doi:10.1021/ol501464e

Enantioselective rhodium-catalyzed arylation of cyclic N-sulfamidate alkylketimines: a new access to chiral β-alkyl-β-aryl amino alcohols

Org Lett. 2014 Jun 20;16(12):3400-3. doi: 10.1021/ol501464e. Epub 2014 Jun 12.

Authors

Ya-Jing Chen¹, Ya-Heng Chen, Chen-Guo Feng, Guo-Qiang Lin

Affiliation

¹ CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032, P. R. China.

PMID: 24922499
DOI: 10.1021/ol501464e

Abstract

The enantioselective rhodium-catalyzed 1,2-addition of arylboronates to cyclic N-sulfamidate alkylketimines was developed. With a rhodium/diene complex as catalyst, high enantioselectivity and broad functional group tolerance were observed. The resulting sulfamidates can easily be converted into chiral β-alkyl-β-aryl amino alcohols.