Rh‐Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to 3‐Arylpropenoates: Enantioselective Synthesis of (R)‐Tolterodine. Issue 6 (27th December 2018)

• Record Type: Journal Article
• Authors: Zullo, Valerio; Iuliano, Anna
• Is Part Of: European journal of organic chemistry. Issue 6(2019)
• Page Start: 1377
• Page End: 1384
• Publication Date: 2018-12-27
• Subjects: Asymmetric catalysis -- P‐ligands -- Steroids -- Chiral pool -- Chiral auxiliaries; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801690
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A highly enantioselective conjugate addition of arylboronic acids to 3‐arylpropenoates is presented. The rhodium complexes obtained from deoxycholic acid derived binaphthyl phosphites showed good activity as well as very high enantioselectivity ( ee up to 99 %) in the conjugate addition to different ethyl‐3‐arylpropenoates, allowing to obtain useful chiral building blocks for the synthesis of active pharmaceutical ingredients. The method was applied to the enantioselective synthesis of the antimuscarinic drug ( R )‐tolterodine. Abstract : Deoxycholic acid derived binaphthyl phosphites promote a highly enantioselective Rh‐catalyzed conjugate addition of arylboronic acids to 3‐arylpropenoates, giving useful chiral building blocks for the synthesis of biologically active compounds. The protocol was successfully applied to the enantioselective synthesis of the antimuscarinic drug ( R )‐tolterodine.