Synfacts 2007(7): 0772-0772  
DOI: 10.1055/s-2007-968693
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

1,4-Addition Reactions Catalyzed by Polymer-Supported Azidoproazaphosphatrane

Contributor(s): Yasuhiro Uozumi, Hiroe Takenaka
C. R. V. Reddy, J. G. Verkade*
Iowa State University, Ames, USA
Further Information

Publication History

Publication Date:
22 June 2007 (online)

Significance

Merrifield resin-bound azidoproaza­phosphatrane 3 catalyzed the 1,4-addition reactions. Catalyst 3 was prepared from azidomethyl resin 2 with proazaphosphatrane 1 (eq. 1). The reaction of 2-nitropropane with methyl acrylate was carried out in the presence of catalyst 3 to give methyl 4-methyl-4-nitropenta­noate in 95% yield (eq. 2). Similarly, several structurally varying Michael donors, such as 1-nitropropane, nitrocycloalkanes, an α-nitroketone, α-keto esters, thio­phenol, diethyl malonate, and ethyl cyanoacetate, underwent Michael addition with a variety of Michael acceptors including methyl crotonate, methyl acrylate, cyclohexenone, methyl vinyl ketone, and acrylonitrile to give the corresponding 1,4-addition products in 67-98% yield.