Multi-step reaction with 10 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C
2.1: dilithium tetrachlorocuprate / tetrahydrofuran / 1.5 h / 0 °C
3.1: sodium periodate / tetrahydrofuran; water / 7.5 h / 20 °C
4.1: sodium hydride / tetrahydrofuran; dimethyl sulfoxide; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere
5.1: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); water; acetic acid / tetrahydrofuran / 17.5 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C
6.2: 1 h / -50 - -45 °C
6.3: 2 h / -70 - 0 °C
7.1: 2,6-dimethylpyridine; N-Bromosuccinimide; silver perchlorate / water; acetone / 0 - 0 h / 0 °C
8.1: samarium diiodide / tetrahydrofuran / 0.83 h / -20 °C
9.1: hydrogenchloride / methanol / 0.5 h / 20 °C
10.1: 2 h / 20 °C
With
2,6-dimethylpyridine; hydrogenchloride; sodium periodate; N-Bromosuccinimide; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); n-butyllithium; samarium diiodide; dilithium tetrachlorocuprate; water; silver perchlorate; sodium hydride; acetic acid; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; mineral oil;
4.1: Corey-Chaykovsky reaction / 5.1: Jacobsen hydrolytic kinetic resolution / 6.3: Brook rearrangement / 8.1: Evans-Tishchenko reduction;
DOI:10.1002/anie.201108692