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Direct Catalytic Enantio‐ and Diastereoselective Mannich Reaction of Isocyanoacetates and Ketimines
Author(s) -
Ortín Irene,
Dixon Darren J.
Publication year - 2014
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.201309719
Subject(s) - catalysis , chemistry , reactivity (psychology) , cinchona , carbon atom , enantioselective synthesis , mannich reaction , organic chemistry , oxide , combinatorial chemistry , medicinal chemistry , ring (chemistry) , medicine , alternative medicine , pathology
A catalytic asymmetric synthesis of imidazolines with a fully substituted β‐carbon atom by a Mannich‐type addition/cyclization reaction of isocyanoacetate pronucleophiles and N ‐diphenylphosphinoyl ketimines has been developed. When a combination of a cinchona‐derived aminophosphine precatalyst and silver oxide was employed as a binary catalyst system, good reactivity, high diastereoselectivities (up to 99:1 d.r.), and excellent enantioselectivities (up to 99 % ee ) were obtained for a range of substrates.