D. A. Evans Diastereoselective Peracid Epoxidation Chem 206 Epoxidation of Cyclic Olefins with Amide Urethane Directing Groups Epoxidation of Cyclic Homoallylic Alcohols Substrate Major Product lectivity Substrate Product Selectivity selective selective r aR= NH2 bR= NH CR= NMe2 ar=ocoNHBn >20: 1 bR=OCONMe? >20 a r= conh 6:1 5:1 bR= CONHE Conditions: Perbenzoic acid, or meta-chloroperbenzoic acid onditions: perbenzoic acid. or meta-chlorobenzoic acid in benzer n benzene or cyclopentane (Table 11, p1316, from the Evans, Hoveyda, Fu review article) (able 14, p1318, from the Evans, Hoveyda, Fu review article)Conditions: Perbenzoic acid, or meta-chloroperbenzoic acid in benzene or cyclopentane. O HN Ph O HN Ph O HO HO HN Me O O HN HO HO Me O O R O O O R O Me R R Me O AcO RO AcO O RO OH O OH Me Et Me HO OH OH HO O Et Me Me HO Me O HO Me O Me HO O Me HO Me HO Me HO AcO HOH2C O AcO HOH2C (Table 14, p1318, from the Evans, Hoveyda, Fu review article) Major Selectivity Product Substrate 9 : 1 "highly selective" 16 : 1 1 : 1 5 : 1 21 : 1 Epoxidation of Cyclic Homoallylic Alcohols (Table 11, p1316, from the Evans, Hoveyda, Fu review article) Conditions: Perbenzoic acid, or meta-chlorobenzoic acid in benzene. "highly selective" "highly selective" Substrate Major Product Selectivity 10 : 1 3 : 1 5 : 1 a. R = NH2 b. R = NHBn c. R = NMe2 >20 : 1 >20 : 1 a. R = OCONHBn b. R = OCONMe2 a. R = CONH2 6 : 1 b. R = CONHBn c. R = CONMe2 >10 : 1 2 : 1 Epoxidation of Cyclic Olefins with Amide &Urethane Directing Groups D. A. Evans Diastereoselective Peracid Epoxidation Chem 206