Short enantioselective syntheses of trans-5-alkylprolines from new functionalized amino alcohols.
Amino alcohols, having an enol ether function, cyclized in acidic medium to give quantitatively diastereosomerically pure bicyclic compounds that were transformed in five steps in enantiopure trans-5-alkylproline derivatives.
Université Pierre et Marie Curie-Paris 6, Laboratoire de Chimie Organique UMR 7611, Institut de Chimie Moléculaire FR 2769, 4 place Jussieu, case courrier 47, 75005 Paris, France.
Jeanne
J
Alladoum
Sylvain
S
Roland
Emmanuel
E
Vrancken
Pierre
P
Mangeney
Catherine
C
Kadouri-Puchot
D000605:Amino Alcohols / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D000605:Amino Alcohols; D001643:Bridged Bicyclo Compounds; D011392:Proline