Jean-Pierre Célérier

Total synthesis of (+) monomorine I from chiral cyclic β-enamino ester

Abstract We describe the total synthesis of (+) Monormorine I 1 and the preparation of cis 2,5 disubstituted functionalized pyrrolidines via cyclic β-enamino esters 4, starting from (S)-pyroglutamic acid.

Enantioselective syntheses of Monomorium minutum ant venom alkaloids : (5R)-2-(5-Hexenyl)-5-nonyl-3,4-dihydro-2H-pyrrole and (2R,5R)-2-(5-hexenyl)-5-nonylpyrrolidine from (s)-pyroglutamic acid.

Abstract We describe enantioselective syntheses of 2,5-disubstituted pyrroline and pyrrolidine with unsaturated radical, starting from (S)-pyroglutamic acid.

Syntheses from chiral heterocyclic β-amino esters. A new versatile access to pyrrolizidine and quinolizidine alkaloids

Abstract Chiral heterocyclic β-amino esters can be easily transformed into bicyclic alkaloids after a diastereoselective alkylation followed by specific chemical transformations.

A NEW DIASTEREOSELECTIVE ROUTE TO 5-SUBSTITUTED-8 -METHYLINDOLIZIDINES. SYNTHESIS OF INDOLIZIDINE (-) 209B

The highly diastereoselective synthesis of the indolizidine alkaloid (−) 209B is described via the diastereoselective alkylation of a chiral cyclic β-amino ester prepared from (R)-methylbenzylamine.

Decarboxylation of cyclic β-enaminoketoesters with boric acid

Abstract Cyclic β-enaminoketoesters prepared by condensation between lactim ethers and β-ketoesters are decarboxylated without deacylation by thermolysis in presence of boric acid to lead stereospecifically to cyclic β-enaminones.

Cyclic β-enaminoesters decarboxylation with boric acid: A convenient synthesis of cyclic imines

Abstract Δ1-pyrrolines, Δ1-piperideines and 1-aza 1-cycloheptenes are formed in good yields from the decarboxylation of alkylated cyclic β-enaminoesters with boric acid.

Enantioselective synthesis of indolizidine (−) 237A [(3R,5S,8aR)-3-butyl-5-(1-oxopropyl)-octahydroindolizine]

Abstract A highly enantioselective synthesis of the indolizidine alkaloid (−) 237A is described via the diastereoselective reduction of a heterocyclic enamine.

Asymmetric synthesis with chiral hydrogenolysable amines. Cyclic β-enamino ester reduction a diastereoselective route to 2,3-disubstituted pyrrolidines

Abstract Cyclic β-enamino esters prepared from chiral α-methylbenzylamines are catalytically reduced with high a diastereoisomeric excess.

Thermolyse des β-énaminodiesters cycliques: Accès à divers β-énaminoesters, β-énaminothioesters et β-enaminoamides.

Abstract A new synthesis of β-enaminoesters, β-enaminothioesters et β-enaminoamides by thermic decomposition of β-enaminodiesters is described.

Enantioselective synthesis of (−)-indolizidine 239AB [(3R,5S,8aR)-3-butyl-5-(3-hydroxypropyl)-octahydroindolizine]

Abstract A highly enantioselective synthesis of the indolizidine alkaloid 239AB is described via the diastereoselective reduction of a chiral cyclic β-enamino ester prepared from (S)-pyroglytamic acid.