Practical one-step synthesis of ethynylglycine synthon from Garner's aldehyde

Patrick Meffre (1) , Sébastien Hermann , Philippe Durand (2) , Gianna Reginato (3) , Antonella Riu

1 SSOPN - Synthèses sélective organique et produits naturels
2 CCD - Communications Cellulaires et Différenciation
3 ICCOM - Istituto di Chimica dei Composti Organometallici

A simple, ef®cient and practical synthesis of (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine (ethynylglycine synthon) is described. The method involves in situ formation of dimethyl 1-diazo-2-oxopropyl phosphonate from dimethyl 2-oxopropyl phosphonate and 4-acetamidobenzene sulfonyl azide and one-pot reaction on Garner's aldehyde. The reaction has been extended to other aminoaldehydes.

Domaines: Chimie; Chimie organique

Patrick Meffre, Sébastien Hermann, Philippe Durand, Gianna Reginato, Antonella Riu. Practical one-step synthesis of ethynylglycine synthon from Garner's aldehyde. Tetrahedron, 2002, 58 (25), pp.5159-5162. ⟨10.1016/S0040-4020(02)00438-6⟩. ⟨hal-02002686⟩