Lithiated alkylidenebis(phosphonates): Reactive phosphorus intermediates in the synthesis of 3‐amino‐1‐alkenylphosphonates

Abstract

An efficient and stereoselectivesynthesis of 3-amino-1-alkenylphosphonates by a direct procedure involving alkylidene diphosphorylation of nucleophiles followed by a Horner-Emmons olefination of aminoaldehydes is reported. The versatility of the method is illustrated by the preparation of P -monoglycosyl-, P-diglycosyl 3-aminoalkenyl-, and alkylphosphonates. C

Application of tris(trimethylsilyl) phosphite as convenient phosphorus nucleophile in the direct synthesis of tetrasubstituted α-aminophosphonic acids from ketimines

“…It is well known that heterocyclic derivatives are a prevalent motif in natural compounds and are well known to play a pivotal role in the design of scaffolds and probes for pharmaceutical applications. [6][7][8] As a part of our continuing interest in organophosphorus chemistry [9][10][11][12] and particularly in the synthesis of new α-functionalized phosphonates and corresponding phosphonic acids [13][14][15][16][17][18] we decided to embark on a project aiming at development of an effective and mild protocol for the synthesis of tetrasubstituted α-aminophosphonic acids. We report herein the addition of tris(trimethylsilyl) phosphite to various N-benzyl ketimines as a very useful direct method, which affords desired α-aminophosphonic acids with good overall yields and under mild reaction conditions.…”