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Iridium‐Catalyzed Chemoselective and Enantioselective Hydrogenation of (1‐Chloro‐1‐Alkenyl) Boronic Esters
Author(s) -
Gazić Smilović Ivana,
CasasArcé Eva,
Roseblade Stephen J.,
Nettekoven Ulrike,
ZanottiGerosa Antonio,
Kovačevič Miroslav,
Časar Zdenko
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106262
Subject(s) - iridium , enantioselective synthesis , chlorine , substituent , chemistry , catalysis , organic chemistry , combinatorial chemistry
Persistent chlorine : Hydrogenation of borolane‐substituted vinylic chlorides catalyzed by IrP N complexes greatly preserved the chlorine substituent on the hydrogenated product, with only 3–19 % of dechlorinated byproducts present after hydrogenation. The α‐chloro boronic ester products are ideal precursors for proteasome‐inhibitor‐type anti‐cancer drugs, a fact which demonstrates the utility of this hydrogenation method.