Catalytic asymmetric sulfenylation to structurally diverse dithioketals

Kui Liao; Feng Zhou; Jin-Sheng Yu; Wei-Ming Gao; Jian Zhou

doi:10.1039/c5cc07010d

Catalytic asymmetric sulfenylation to structurally diverse dithioketals

Chem Commun (Camb). 2015 Nov 21;51(90):16255-8. doi: 10.1039/c5cc07010d.

Authors

Kui Liao¹, Feng Zhou², Jin-Sheng Yu¹, Wei-Ming Gao¹, Jian Zhou³

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062, China.
² Department of Chemistry, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China. fzhou@chem.ecnu.edu.cn and Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Chemical Engineering, East China Normal University, Shanghai, 200062, China.
³ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062, China and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, P. R. China.

PMID: 26399606
DOI: 10.1039/c5cc07010d

Abstract

We report the first example of the highly enantioselective synthesis of structurally diverse chiral dithioketals via asymmetric sulfenylation of various types of S-based nucleophiles, catalyzed by a cheap cinchona alkaloid derivative, dihydroquinine.

Publication types

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

MeSH terms

Catalysis
Molecular Structure
Quinidine / analogs & derivatives*
Quinidine / chemistry
Sulfinic Acids / chemistry*
Toluene / analogs & derivatives*
Toluene / chemical synthesis
Toluene / chemistry

Substances

Sulfinic Acids
Toluene
hydroquinidine
Quinidine
dithiol