Thiophostone‐Derived Brønsted Acids in the Organocatalyzed Transfer Hydrogenation of Quinolines: Influence of the P‐Stereogenicity. Issue 1 (24th October 2013)

• Record Type: Journal Article
• Authors: Ferry, Angélique; Stemper, Jérémy; Marinetti, Angela; Voituriez, Arnaud; Guinchard, Xavier
• Is Part Of: European journal of organic chemistry. Issue 1(2014)
• Page Start: 188
• Page End: 193
• Publication Date: 2013-10-24
• Subjects: Chirality -- Phosphorus -- Organo­catalysis -- Heterocycles -- Brønsted acids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301253
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new approach to Brønsted acid organocatalysis is described and is based on the use of thiophosphonic acids possessing both a chiral backbone and a chiral phosphorus function. The influence of the phosphorus stereochemistry on the enantioselectivity proved to be crucial in the hydrogen transfer hydrogenation of 2‐phenylquinoline with Hantzsch esters. Abstract : The synthesis and catalytic activities of P‐chiral Brønsted acids possessing a thiophostone‐derived skeleton are described. The stereochemical outcome of the test reaction is strongly dependant on the stereochemistry of the phosphorus atom.