Substituted cyclopentenes, their preparation and their use...

Details Substituted cyclopentenes, their preparation and their use... Substituted cyclopentenes, their preparation and their use...

C - Chemistry, Metallurgy

07

C

C07C 271/56 (2006.01) C07C 227/32 (2006.01) C07C 229/48 (2006.01) C07D 263/52 (2006.01)

Patent

CA 2380656

3,4-Disubstituted-1-cyclopentene compounds, in substantially enantiopure form, have the relative stereochemistry according to formula (1A) or (1B) including the opposite enantiomers thereof, wherein R1 is either COOX, wherein X is alkyl, H or a salt-forming cation, or CH2OH, wherein the hydroxyl group is optionally protected; R2 is H or a protecting group; R3 is H or alkyl; and R4 is H, alkoxy, alkyl, aryl or aralkyl; or, in the case of formula 1A, R2 and R4 are linked to form an oxazolidinone ring. These compounds can be used to prepare a series of complementary stereochemically varied cyclopentane scaffolds.

Composés de 1-cyclopentène-3,4-disubstitué sous forme énantiomère pratiquement pure et possédant la stéréochimie relative illustrée par la formule (1A) ou (1B) y compris leurs énantiomères opposés, dans laquelle R?1¿ représente CCOX, X représentant alkyle, H ou un cation formant un sel, soit CH¿2?OH, dans laquelle le groupe hydroxyle est éventuellement protégé; R?2¿ représente H ou un groupe protecteur; R?3¿ représente H ou alkyle; R?4¿ représente H, alcoxy, alkyle, aryle ou aralkyle; ou, dans le cas de la formule 1A, R?2¿ et R?4¿ sont liés afin de constituer un noyau d'oxazolidinone. On peut utiliser ces composés afin de préparer une série d'ossatures de cyclopentane complémentaires présentant des variations stéréochimiques.

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