Dynamic kinetic resolution of racemic beta-haloalcohols: Direct access to enantioenriched epoxides

Haak RM; Berthiol F; Jerphagnon T; Gayet AJA; Tarabiono C; Postema CP; Ritleng V; Pfeffer M; Janssen DB; Minnaard AJ; Feringa BL; de Vries JG

Journal of the American Chemical Society, Vol.130, No.41, 13508-13508, 2008

Haak RM, Berthiol F, Jerphagnon T, Gayet AJA, Tarabiono C, Postema CP, Ritleng V, Pfeffer M, Janssen DB, Minnaard AJ, Feringa BL, de Vries JG

The direct chemo-enzymatic DKR of racemic beta-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the haloalcohol is achieved using the new iridacycle 3, one of the most effective racemization catalysts to date for beta-haloalcohols.