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Enantioselective Iridium‐Catalyzed Allylic Substitution with 2‐Methylpyridines
Author(s) -
Liu XiJia,
You ShuLi
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700433
Subject(s) - enantioselective synthesis , allylic rearrangement , iridium , chemistry , catalysis , pyridine , combinatorial chemistry , nucleophile , nucleophilic substitution , substitution (logic) , organic chemistry , computer science , programming language
Abstract An enantioselective iridium‐catalyzed allylic substitution with a set of highly unstabilized nucleophiles generated in situ from 2‐methylpyridines is described. Enantioenriched 2‐substituted pyridines, which are frequently encountered in natural products and pharmaceuticals, could be easily constructed by this simple method in good yields and excellent enantioselectivity. The synthetic utility of the pyridine products is demonstrated through the synthesis of a key intermediate of a reported Na + /H + exchanger inhibitor and the total synthesis of (−)‐lycopladine A.