Direct Catalytic Enantio‐ and Diastereoselective Mannich Reaction of Isocyanoacetates and Ketimines | Zendy

Ortín Irene | Zendy; Dixon Darren J. | Zendy

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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.

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