Enantioselective synthesis of β-aryloxycarboxylic esters via asymmetric hydrogenation of β-aryloxy-α,β-unsaturated esters.
A novel synthesis of β-aryloxycarboxylic esters via asymmetric hydrogenation of the corresponding β-aryloxy-α,β-unsaturated esters has been demonstrated. Bis(norbornadiene)rhodium(I) tetrafluoroborate (1 mol %) and Walphos W008-1 were used to generate the saturated products with high enantioselectivity and in high yield. The tolerability of the reaction to a diverse range of substituents on the aromatic ring was also explored.
Global Process Chemistry, Merck Sharp and Dohme Research Laboratories, Hertford Road, Hoddesdon, Hertfordshire, EN11 9BU, United Kingdom. gavin_stewart@merck.com
Gavin W
GW
Stewart
Michael
M
Shevlin
Adam D Gammack
AD
Yamagata
Andrew W
AW
Gibson
Stephen P
SP
Keen
Jeremy P
JP
Scott
D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D006865:Hydrogenation; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D001555:Benzene Derivatives; D002264:Carboxylic Acids; D004952:Esters; D012238:Rhodium