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Synfacts 2007(8): 0879-0879  
DOI: 10.1055/s-2007-968803
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Propargyl Amines with Immobilized Cu(Pybox) Complexes

Contributor(s): Yasuhiro Uozumi, Yutaka Matsuura
C. McDonagh, P. O’Conghaile, R. J. M. Klein Gebbink, P. O’Leary*
National University of Ireland, Galway, Ireland and Utrecht University, The Netherlands
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

Copper(I) and copper(II) complexes of bis(oxazolinyl)pyridine (Pybox) were immobilized on silica via electrostatic interactions by mixing silica supports and Cu(Pybox) triflates. The immobilized catalysts 1 and 2 were used in the direct asymmetric addition of terminal alkynes to imines leading to propargyl amines with enantiomeric purity of up to 81% ee. The immobilized Cu catalysts were reused three times with slight loss of activity (catalyst 1: 98-91%, 47.5-35.5% ee; catalyst 2: 99-52%, 81.5-79% ee).