Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides

Naifu Hu; Guoqing Zhao; Yuanyuan Zhang; Xiangqian Liu; Guangyu Li; Wenjun Tang

doi:10.1021/jacs.5b03760

Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides

J Am Chem Soc. 2015 Jun 3;137(21):6746-9. doi: 10.1021/jacs.5b03760. Epub 2015 May 18.

Authors

Naifu Hu¹, Guoqing Zhao¹, Yuanyuan Zhang¹, Xiangqian Liu¹, Guangyu Li¹, Wenjun Tang¹

Affiliation

¹ State Key Laboratory of Bio-Organic and Natural Products Chemistry and Collaborative Innovation Center of Chemistry for life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China.

PMID: 25938599
DOI: 10.1021/jacs.5b03760

Abstract

The rhodium-catalyzed asymmetric hydroboration of α-arylenamides with BI-DIME as the chiral ligand and (Bpin)2 as the reagent yields for the first time a series of α-amino tertiary boronic esters in good yields and excellent enantioselectivities (up to 99% ee).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Boronic Acids / chemical synthesis*
Boronic Acids / chemistry
Esters / chemical synthesis*
Esters / chemistry
Molecular Structure
Stereoisomerism

Substances

Amides
Boronic Acids
Esters