Guy Duguay

Synthesis and properties of new 2-mono and 2,3-bis(hydroxymethyl)-6,7-ethylenedithio TTF vinylogs

Abstract The synthesis of title compounds prone to generate hydrogen bonds thanks to their alcohol functionalities is depicted. Cyclic voltammetry proves these derivatives to be strong π-donors, able to act as convenient precursors of related organic metals.

THIA-1 AZA-3 BUTADIENES SUBSTITUES: ACTION DU CETENE ET DERIVES

Abstract Novel, diversely substituted 1-thia 3-aza butadienes have been prepared and reacted with ketene or its derivatives. Via a general (4 + 2) cycloaddition reaction, they afford functionalised 6H-1,3-thiazine 6-ones, the electrophilic properties of which are described. This cycloaddition gives rise to other reaction products resulting from the addition of two or three molecules of ketene according to the nature of the substituents.

Synthese de structures á carbone multifonctionnalise derivees de cyano-2 glycinates N-proteges

Abstract Some multifunctional carbon compounds derivated from N-protected cyano-2 glycinates are easily obtained in good yields using anionic or cationic glycine equivalent strategy. They are versatile building blocks for the synthesis of natural products.

Resolution of multifunctional carbon compounds derivated from N-protected 2-cyano glycinates

Abstract Synthesis and resolution of covalent diastereoisomers from some N-protected 2-cyanoglycinates using (S)-(−)-ethyl lactate as a resolving reagent, give rise after transesterification with titanium tetraisoproposide, to chiral multifunctional carbon compounds 1 , valuable chiral auxiliaries as key precursors in organic synthesis.

Control of the enantiomeric purity and correlation with the absolute configuration of N-protected 2-cyanoglycinates

Abstract The enantiomeric purity of substituted N-phthaloyl-2-cyanoglycine methyl esters obtained by resolution of covalent diastereoisomers was easily established by measuring the shift separation of signals using Eu(hfc)3. A correlation with the absolute configuration of enantiomers was observed.

Synthese d'(alkoxycarbonyl-4 methyl-5 dihydro-3,6 2h-thiazine-i,3 yl-2)-2 amino-2 methoxy-2 glycinates n-proteges, precurseurs potentiels de cephamycines, par deux voies differentes

Abstract Diastereoisomeric couples of α-methoxy α-dihydrothiazinyl glycinates 1 were obtained by two different ways, with a proof of structure by X-Ray. 3,6-Dihydro-2H-1, 3-thiazine rings were obtained via (3+3) and (4+2) cyclocondensations, followed by regioselective reduction. These dihydrothiazine derivatives are potential precursors of cephamycins.

α-Methoxy-α-(6H-1,3-thiazin-2-yl)glycinates precursors of 7-methoxycephems by [3+3] cyclocondensation reaction

Abstract We report here a new widely useful and applicable preparation of functionalised 6H-1,3-thiazinic cycloadducts, versatile key intermediates in the total multistep syntheses of 7-methoxycephems (as analogues of 7-methoxycephalosporins).