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Synfacts 2007(9): 0998-0998  
DOI: 10.1055/s-2007-968923
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Polyisobutylene-Supported Reusable Soluble Catalysts

Contributor(s): Yasuhiro Uozumi, Hiroe Takenaka
D. E. Bergbreiter*, J. Tian
Texas A&M University, College Station, USA
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

Polyisobutylene oligomers (PIB)-supported Rh(II) catalyst 1 and chiral bisoxazoline Cu(I) catalyst 2 were prepared and used in cata­lytic olefin cyclopropanation reactions. Thus, the cyclopropanation of styrene with ethyldiazoacetate in the presence of 1 mol% catalyst 1 in heptane at 25 °C gave cis- and trans-cyclopropane products in 53% yield (trans/cis = 59:41) (eq. 1). Chiral bisoxazoline Cu(I) catalyst 2 demonstrates a high diastereoselectivity (trans/cis = 81:91) and good enantioselectivity in both trans and cis products (92% ee and 68% ee, respectively) in otherwise the same reaction system.