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. 2014 Dec 18;13(7):2092–2099. doi: 10.1039/c4ob02318h

Table 2. Application scope of the asymmetric epoxidation using amide 6C .

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Entry R Ald. Prod. Cond. a Yield b [%] dr c [%]
1 Ph 2a 17a A 78 >98
2 B 73 >98
3 4-MeC6H4 2b 17b A 80 >98
4 2-MeC6H4 2c 17c A 79 >98
5 4-ClC6H4 2d 17d A 75 >98
6 4-BrC6H4 2e 17e A 85 >98
7 4-PhC6H4 2f 17f A 89 >98
8 4-MeOC6H4 2g 17g A 73 >98
9 4-Me2NC6H4 2h 17h B (60) d >98
10 4-CNC6H4 2i 17i C 62 >98
11 3-NO2C6H4 2j 17j C 68 >98
12 n-Decyl– 2k 17k D 42 >98
13 Cyclohexyl– 2l 17l D 39 >98

aA: i-PrOH, 25 °C, 24 h, Cs2CO3 (s, 20 eq.); B: toluene, 60 °C, 24 h, Cs2CO3 (s, 20 eq.); C: toluene, 25 °C, 72 h, Cs2CO3 (s, 20 eq.); D: toluene, 25 °C, 24 h, Cs2CO3 (s, 20 eq.).

bIsolated yield.

cDetermined by 1H NMR of the crude reaction mixture.

dFull decomposition on silica gel, crude NMR yield given in brackets.