Highly efficient kinetic resolution of beta-halohydrins catalyzed by a chiral 1,2-diamine.
Kinetic resolution of racemic beta-halohydrins has been achieved by reaction with benzoyl chloride in the presence of a catalytic amount (0.3 mol%) of a chiral diamine combined with diisopropylethylamine to afford the corresponding benzoates and unreacted beta-halohydrins in good to excellent enantioselectivities. The benzoate can be converted to the corresponding allylic benzoate without loss of optical purity by treatment with (1,5-diazabicyclo[4.3.0]non-5-ene).
Sano
T
T
Faculty of Science, Ibaraki University, Mito, Japan.
Miyata
H
H
Oriyama
T
T
D000215:Acylation; D001565:Benzoates / Q000737:chemistry; D001969:Bromobenzenes / Q000737:chemistry*; D003511:Cyclohexanols / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D054833:Isoindoles; D009904:Optical Rotation; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
C408482:1,2-dihydro-2-(1-methylpyrrolidin-2-yl)isoindole; D001565:Benzoates; D001969:Bromobenzenes; D003511:Cyclohexanols; D005021:Ethylamines; D007211:Indoles; D054833:Isoindoles; D011759:Pyrrolidines; C016162:triethylamine; C013409:benzoyl chloride