Multi-step reaction with 10 steps
1.1: sodium hydride / nujol; tetrahydrofuran / 16.5 h / 0 °C
1.2: 3.3 h / 0 °C
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux
3.1: (R)-Tol-BINAP; tetrabutylammonium triphenyldifluorosilicate; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran / 16 h / -78 °C
4.1: methanol; toluene / 1 h / 110 °C / Sealed tube
5.1: tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 18 h / -35 °C
6.1: zinc(II) chloride / tetrahydrofuran / 3 h / Molecular sieve; Reflux
7.1: silver(l) oxide / diethyl ether / 1 h / Molecular sieve; Reflux
8.1: trimethylaluminum / toluene; dichloromethane / 0.58 h / 0 °C
8.2: 1.17 h / 0 °C
9.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C
10.1: triethylamine; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper(l) iodide; triphenylphosphine / N,N-dimethyl-formamide / 9 h / 60 °C
With
2,6-dimethylpyridine; copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; (R)-Tol-BINAP; trimethylaluminum; copper(II) bis(trifluoromethanesulfonate); sodium hydride; acetic acid; triethylamine; triphenylphosphine; tetrabutylammonium triphenyldifluorosilicate; zinc(II) chloride; silver(l) oxide; tetramethylammonium triacetoxyborohydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; nujol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
3.1: |Mukaiyama Aldol Addition;
DOI:10.1039/c3ob27508f