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Highly Selective Iridium‐Catalyzed Asymmetric Hydrogenation of Trifluoromethyl Olefins: A New Route to Trifluoromethyl‐ Bearing Stereocenters
Author(s) -
Engman Mattias,
Cheruku Pradeep,
Tolstoy Päivi,
Bergquist Jonas,
Völker Sebastian F.,
Andersson Pher G.
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800645
Subject(s) - stereocenter , trifluoromethyl , chemistry , iridium , enantioselective synthesis , asymmetric hydrogenation , catalysis , fluorine , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , alkyl
Fluorine‐containing compounds are useful in many applications ranging from pharmaceuticals to ferroelectric crystals. We have developed a new, highly enantioselective synthetic route to trifluoromethyl‐bearing stereocenters in up to 96% ee via asymmetric hydrogenation using N,P‐ligated iridium catalysts. We also hydrogenated an isomeric mixture of olefins; this reaction gave the hydrogenation product highly enantioselectively (87% ee ), and only the E isomer was present after the reaction had reached 56% conversion.