Premium
Rh‐Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to 3‐Arylpropenoates: Enantioselective Synthesis of (R)‐Tolterodine
Author(s) -
Zullo Valerio,
Iuliano Anna
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801690
Subject(s) - enantioselective synthesis , chemistry , tolterodine , conjugate , catalysis , rhodium , stereochemistry , combinatorial chemistry , organic chemistry , overactive bladder , medicine , mathematical analysis , alternative medicine , mathematics , pathology
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.