Synthesis of compounds with predetermined chirality

Details Synthesis of compounds with predetermined chirality Synthesis of compounds with predetermined chirality

C - Chemistry, Metallurgy

07

C

C07C 233/17 (2006.01) C07C 29/147 (2006.01) C07C 31/125 (2006.01) C07C 33/20 (2006.01) C07C 45/41 (2006.01) C07C 45/45 (2006.01) C07C 45/65 (2006.01) C07C 45/67 (2006.01) C07C 47/02 (2006.01) C07C 47/228 (2006.01) C07C 49/213 (2006.01) C07C 49/76 (2006.01) C07C 49/782 (2006.01) C07C 51/06 (2006.01) C07C 53/126 (2006.01) C07C 57/30 (2006.01) C07C 227/18 (2006.01) C07C 227/32 (2006.01) C07C 231/12 (2006.01) C07C 231/18 (2006.01) C07C 233/18 (2006.01) C07C 233/22 (2006.01) C07C 235/02 (2006.01) C07C 235/34 (20

Patent

CA 2184500

A method for synthesizing enantionmerically enriched chemical intermediates with predetermined chirality is described. The method comprises formation of a pseudoephedrine amide, followed by stereoselective alkylation at the .alpha. carbon. The chiral auxiliary can then be cleaved off, affording chiral end products useful for further transformations. The enantiomeric enrichment of the chiral end products may exceed 98 %, and the chiral auxiliary can be recovered. Novel amides of pseudoephedrine used in this method are also disclosed.

Un procédé qui permet de synthétiser des intermédiaires chimiques enrichis par voie énantiomère et dotés d'une chiralité prédéterminée, consiste à obtenir un amide de pseudoéphédrine puis à pratiquer une alkylation stéréosélective au niveau du carbone .alpha.. On peut alors scinder l'auxiliaire chiral, ce qui fournit des produits finals chiraux utiles pour des transformations ultérieures. L'enrichissement énantiomère des produits finals chiraux peut dépasser 98 % et on peut récupérer l'auxiliaire chiral. On décrit aussi de nouveaux amides de pseudoéphédrine utilisés dans le cadre de ce procédé.

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