Multi-step reaction with 10 steps
1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C
2.1: (1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol / toluene; hexane / 24 h / 0 °C
3.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C
4.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C
5.1: triphenylphosphine / dichloromethane / 0.5 h / -15 °C
5.2: 1 h / -20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C
6.2: 2 h / -78 °C
6.3: 20 h / -78 - 20 °C
7.1: silver(I) triflimide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); N-iodo-succinimide / acetone; water / 5 h / -15 - 20 °C
8.1: palladium diacetate; tetraethylammonium chloride; trifuran-2-yl-phosphane / toluene / 6 h / 90 °C / 2280.15 Torr / Molecular sieve
9.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C
10.1: dichloromethane / 1 h / 20 °C / Molecular sieve
10.2: 24 h / -30 °C
With
pyridine; 2,6-dimethylpyridine; N-iodo-succinimide; n-butyllithium; trifuran-2-yl-phosphane; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); hydrogen fluoride; tetraethylammonium chloride; palladium diacetate; sulfur trioxide pyridine complex; diisobutylaluminium hydride; (1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; silver(I) triflimide;
In
tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene;
6.1: |Corey-Fuchs Alkyne Synthesis / 6.2: |Corey-Fuchs Alkyne Synthesis;
DOI:10.1021/jacs.6b07585