Synthesis of optically active alpha-methyl beta-hydroperoxy esters by diastereoselective singlet oxygen ene reaction and horseradish peroxidase catalyzed kinetic resolution
W. Adam et al., Synthesis of optically active alpha-methyl beta-hydroperoxy esters by diastereoselective singlet oxygen ene reaction and horseradish peroxidase catalyzed kinetic resolution, MONATS CHEM, 131(6), 2000, pp. 697-705
Optically active diastereomeric beta-hydroperoxy eaters 4 have been prepare
d by singlet oxygen ene reaction of beta,gamma-unsaturated esters 3 and sub
sequent horseradish peroxidase (HRP) catalyzed kinetic resolution of the en
e product. The highest enantiomeric excess (up to 95%) has been obtained fo
r the isopropyl ester threo-4c, which establishes that the size of the remo
te ester functionality exercises appreciable control in the enantioselectiv
ity of the enzymatic kinetic resolution.