Multi-step reaction with 10 steps
1.1: dilithium tetrachlorocuprate / tetrahydrofuran / 1.5 h / 0 °C
2.1: sodium periodate / tetrahydrofuran; water / 7.5 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; dimethyl sulfoxide; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere
4.1: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); water; acetic acid / tetrahydrofuran / 17.5 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C
5.2: 1 h / -50 - -45 °C
5.3: 2 h / -70 - 0 °C
6.1: 2,6-dimethylpyridine; N-Bromosuccinimide; silver perchlorate / water; acetone / 0 - 0 h / 0 °C
7.1: samarium diiodide / tetrahydrofuran / 0.83 h / -20 °C
8.1: dmap; 2,4,6-trichlorobenzoyl chloride; dihydropyrimidinone / toluene / 7 h / 0 - 20 °C / Inert atmosphere
9.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane / N,N-dimethyl-formamide / 1.5 h
10.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,3,5,6-tetrafluoro-1,4-benzoquinone / toluene / 1.5 h / 90 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium periodate; N-Bromosuccinimide; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); n-butyllithium; samarium diiodide; dilithium tetrachlorocuprate; triphenyl-arsane; 2,3,5,6-tetrafluoro-1,4-benzoquinone; 2,4,6-trichlorobenzoyl chloride; water; silver perchlorate; sodium hydride; acetic acid; dihydropyrimidinone;
In
tetrahydrofuran; hexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; mineral oil;
3.1: Corey-Chaykovsky reaction / 4.1: Jacobsen hydrolytic kinetic resolution / 5.3: Brook rearrangement / 7.1: Evans-Tishchenko reduction / 9.1: Stille coupling;
DOI:10.1002/anie.201108692