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Synfacts 2006(4): 0401-0401
DOI: 10.1055/s-2006-932090
DOI: 10.1055/s-2006-932090
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Merrifield Resin Supported Copper Catalyst for Asymmetric Cyclopropanation
H. Werner, C. I. Herrerías, M. Glos, A. Gissibl, J. M. Fraile, I. Pérez, J. A. Mayoral*, O. Reiser*
Universität Regensburg, Germany and Universitario de Catálisis Homogénea, Zaragoza, Spain
Further Information
Publication History
Publication Date:
24 March 2006 (online)
Significance
A recyclable Merrifield resin supported copper catalyst for asymmetric cyclopropanation of styrene was developed. Aza(bisoxazoline) ligand 1 was attached to the Merrifield resin and the resulting immobilized ligand 2 was evaluated in copper(I)-catalyzed asymmetric cyclopropanation. The cyclopropanation of styrene with ethyl diazoacetate by using Cu(OTf)2·2 (1 mol%) gave the trans/cis isomers of the cyclopropanation products in a 74:26 ratio in 94% yield with 99% ee (trans) and 90% ee (cis), respectively. This supported catalyst was reused without loss of selectivity (see scheme).