Cyclopropyl phosphonates, synthesis

A synthesis of novel (1-amino-l-cyclopropyl)phosphonic acids is initiated by the ring opening of oxiranes by dialkyl (isocyanomethyl)phosphonate carbanions (Scheme 48). The product from the ring opening step is the (3-hydroxy-l-isocyanoalkyl)phosphonic diester 355, which, through its O-mesylate 356, is convertible into the cyclopropyl isocyanide 357 this, with HCl in MeOH, yields the racemic (1-amino-1-cyclopropyl)-phosphonic ester 358 ... 

CuOTf is an outstandingly effective catalyst for the synthesis of cyclopropyl phosphonates by the reaction of diethyl diazomethylphosphonate with alkenes (eq 6). The resulting cyclopropylphosphonates are useful intermediates for the synthesis of alkylidenecyclopropanes by Wadsworth-Emmons alkena-tion with aromatic carbonyl compounds (eq 7). ... 

The synthesis of some cyclopropylcyano phosphonate pyranosides has been described (Scheme 25). (See Vol. 24, p.l67 and Vol.22, p.l50 for a similar preparation of cyclopropyl cyanides.)... 

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