http://onlinelibrary.wiley.com/doi/10.1002/anie.201309719/abstract

Abstract

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.

Angewandte Chemie International Edition

Volume 53, Issue 13, pages 3462–3465, March 24, 2014

Direct Catalytic Enantio- and Diastereoselective Mannich Reaction of Isocyanoacetates and Ketimines^†

1. Dr. Irene Ortín and
2. Prof. Dr. Darren J. Dixon^*

Article first published online: 24 FEB 2014

DOI: 10.1002/anie.201309719

Abstract

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.

Author Information

1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK)

Email: Prof. Dr. Darren J. Dixon (darren.dixon@chem.ox.ac.uk)

^*Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK)===

Professor Darren J. Dixon

Darren.Dixon@chem.ox.ac.uk

http://research.chem.ox.ac.uk/darren-dixon.aspx

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