Multi-step reaction with 11 steps
1: 95 percent / m-CPBA / CH2Cl2 / 20 °C
2: 42 percent / (R,R)-(salen)Co(III)(OAc) / H2O
3: 71 percent / CuI / tetrahydrofuran / 20 °C
4: 92 percent / imidazole / CH2Cl2 / 20 °C
5: 96 percent / m-CPBA / CH2Cl2 / 20 °C
6: 41 percent / (S,S)-(salen)Co(III)(OAc) / H2O
7: 72 percent / n-BuLi; BF3*OEt2 / tetrahydrofuran / -78 °C
8: 87 percent / TBAF / tetrahydrofuran / 20 °C
9: 95 percent / PTSA / CH2Cl2 / 20 °C
10: 85 percent / LAH / tetrahydrofuran / 20 °C
11: 98 percent / imidazole / CH2Cl2 / 20 °C
With
1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; n-butyllithium; (R,R)-(salen)Co(III)(OAc); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; dichloromethane; water;
2: Jacobsen hydrolytic kinetic resolution / 6: Jacobsen hydrolytic kinetic resolution;
DOI:10.1016/j.tetlet.2007.01.056