Catalytic asymmetric hydrogenation

Abstract

Abstract 1. A PROCESS FOR THE ASYMMETRIC HYDROGENATION OF AN OLEFIN WHICH COMPRISES THE HYDROGENATION OF AN OLEFIN OF THE FORMULA R1-C(-R2)=C(-R3)-R4 WHEREIN R1, R2, R3 AND R4 ARE EACH INDEPENDENTLY SELECTED FROM THE GROUP CONSISTING OF HYDROGEN; ALKYL HAVING AT LEAST ONE AND A MACIMUM OF 12 CARBON ATOMS; SUBSTITUTED ALKYL SAID SUBSTITUTION BEING SELECTED FROM THE GROUP CONSISTING OF AMINO, HYDROXY, NITRO, THIO, CARBONYL, CARBOXYL, CARBOXYLIC ESTER, SAID ESTER GROUP HAVING A MAXIMUM OF 6 CARBON ATOMS; PHENYL; SUBSTITUTED PHENYL, SAID SUBSTITUTION BEING SELECTED FROM THE GROUP CONSISTING OF ALKYL HAVING A MAXIMUM OF 4 CARBON ATOMS, AMINO, CARBOXYL, NITRO AND CARBOXYLIC ESTER, SAID ESTER HAVING A MAXIMUM OF 4 CARBON ATOMS, AND SAID SUBSTITUTION BEING LESS THAN 3 SUBSTITUTENTS; AMINO; DIBENZYLAMINO; BENZYLAMINO; NITRO; CARBOXYL AND CARBOXYLIC ESTER, SAID ESTER HAVING A MAXIMUM OF 4 CARBON ATOMS, PROVIDED THAT, UPON HYDROGENATION, (A) THE OLEFIN IS CAPABLE OF FORMING A RACEMIC MIXTURE, AND (B) AT LEAST ONE OF THE CARBON ATOMS UNITED BY THE OLEFINIC BOND IS CAPABLE OF FORMING AN ASYMMETRIC CARBON, IN THE PRESENCE OF A CATALYST REPRESENTED BY THE FORMULA M1XNL3 WHEREIN M1 IS A METAL SELECTED FROM THE GROUP CONSISTING OF RHODIUM, RUTHENIUM AND IRIDIUM; X IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN, CHLORINE, FLUORINE, BROMINE AND IODINE; EACH L IS INDEPENDENTLY SELECTED FROM THE GROUP AR5R6R7, WHEREIN A IS SELECTED FROM THE GROUP CONSISTING OF PHOSPHORUS AND ARSENIC AND R5, R6 AND R7 ARE EACH INDEPENDENTLY SELECTED FROM THE GROUP CONSISTING OF HYDROGEN; ALKYL HAVING AT LEAST ONE CARBON ATOM AND A MAXIMUM OF 12 CARBON ATOMS; SUBSTITUTED ALLKYL, SAID SUBSTITUTION SELECTED FROM THE GROUP CONSISTING OF AMINO, CARBONYL, PHENYL, NITRO AND ALKOXY, SAID ALKOXY HAVING A MAXIMUM OF 4 CARBON ATOMS; PHENYL; SUBSTITUTED PHENYL, SAID SUBSTITUTION SELECTED FROM THE GROUP CONSISTING OF ALKYL HAVING A MAXIMUM OF 4 CARBON ATOMS, AMINO AND NITRO, SAID SUBSTITUTION BEING LESS THAN 3 SUBSTITUENTS; CYCLOALKYL HAVING AT LEAST 3 CARBON ATOMS AND A MAXIMUM OF 6 CARBON ATOMS; PYRRYL; THIENYL; FURYL; PYRIDYL AND PIPERIDYL, PROVIDED THAT AT LEAST ONE L GROUP IS OPTICALLY ACTIVE AND N IS ONE OF THE INTEGERS ONE OR THREE.

Inventors

• 👤 W Knowles
• 👤 M Sabacky

Bibliographic Details