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

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

A simple, efficient 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 sulfony...

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Veröffentlicht in:Tetrahedron 2002-06, Vol.58 (25), p.5159-5162
Hauptverfasser: Meffre, Patrick, Hermann, Sébastien, Durand, Philippe, Reginato, Gianna, Riu, Antonella
Format: Artikel
Sprache:eng
Schlagworte:
aldehydes
alkynes
Chemical Sciences
diazo compounds
ethynyloxazolidine
Organic chemistry
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Zusammenfassung:A simple, efficient 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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00438-6