(R)-(-)-咯利普兰合成路线 （共 64 条）
反应条件
ammonia; lithium in tetrahydrofuran
T=-40°C; 0.166667 h; Title compound not separated from byproducts.;
参考文献
Barluenga, Jose; Fernandez-Rodriguez, Manuel A.; Aguilar, Enrique; Fernandez-Mari, Felix; Salinas, Alejandro; Olano, Bernardo
Chemistry - A European Journal, 2001 , vol. 7, # 16 p. 3533 - 3544
反应条件
1.1: 97 percent / H2SO4 / 6 h / 100 °C
2.1: 99 percent / NBS / acetonitrile / 10 h / 60 °C
3.1: 95 percent / NaHCO3 / methanol / 3 h / Heating
4.1: 89 percent / K2CO3 / dimethylformamide / 12 h / 50 °C
5.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C
5.2: diethyl ether; hexane / 1 h / -78 °C
6.1: 88 percent / Na2CO3; O2 / Pd(OAc)2 / dimethylformamide / 12 h / 50 °C / 760 Torr
7.1: 90 percent / NBS; AIBN / CCl4 / 10 h / Heating
8.1: 99 percent / NaN3 / ethanol; H2O / 8 h / Heating
9.1: NaBH4; [4(S)-Ph-oxazolidin-2-ylidene][4(S)-Ph-2-oxazolin-2-yl](CN)C / CoCl2*6H2O / ethanol; dimethylformamide / 24 h / 25 °C
View Scheme
参考文献
Paraskar, Abhimanyu S.; Sudalai, Arumugam
Tetrahedron, 2006 , vol. 62, # 20 p. 4907 - 4916
反应条件
1: 90 percent / NBS; AIBN / CCl4 / 10 h / Heating
2: 99 percent / NaN3 / ethanol; H2O / 8 h / Heating
3: NaBH4; [4(S)-Ph-oxazolidin-2-ylidene][4(S)-Ph-2-oxazolin-2-yl](CN)C / CoCl2*6H2O / ethanol; dimethylformamide / 24 h / 25 °C
View Scheme
参考文献
Paraskar, Abhimanyu S.; Sudalai, Arumugam
Tetrahedron, 2006 , vol. 62, # 20 p. 4907 - 4916
反应条件
1: 99 percent / NaN3 / ethanol; H2O / 8 h / Heating
2: NaBH4; [4(S)-Ph-oxazolidin-2-ylidene][4(S)-Ph-2-oxazolin-2-yl](CN)C / CoCl2*6H2O / ethanol; dimethylformamide / 24 h / 25 °C
View Scheme
参考文献
Paraskar, Abhimanyu S.; Sudalai, Arumugam
Tetrahedron, 2006 , vol. 62, # 20 p. 4907 - 4916
反应条件
1.1: 99 percent / NBS / acetonitrile / 10 h / 60 °C
2.1: 95 percent / NaHCO3 / methanol / 3 h / Heating
3.1: 89 percent / K2CO3 / dimethylformamide / 12 h / 50 °C
4.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C
4.2: diethyl ether; hexane / 1 h / -78 °C
5.1: 88 percent / Na2CO3; O2 / Pd(OAc)2 / dimethylformamide / 12 h / 50 °C / 760 Torr
6.1: 90 percent / NBS; AIBN / CCl4 / 10 h / Heating
7.1: 99 percent / NaN3 / ethanol; H2O / 8 h / Heating
8.1: NaBH4; [4(S)-Ph-oxazolidin-2-ylidene][4(S)-Ph-2-oxazolin-2-yl](CN)C / CoCl2*6H2O / ethanol; dimethylformamide / 24 h / 25 °C
View Scheme
参考文献
Paraskar, Abhimanyu S.; Sudalai, Arumugam
Tetrahedron, 2006 , vol. 62, # 20 p. 4907 - 4916
反应条件
1.1: 95 percent / NaHCO3 / methanol / 3 h / Heating
2.1: 89 percent / K2CO3 / dimethylformamide / 12 h / 50 °C
3.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C
3.2: diethyl ether; hexane / 1 h / -78 °C
4.1: 88 percent / Na2CO3; O2 / Pd(OAc)2 / dimethylformamide / 12 h / 50 °C / 760 Torr
5.1: 90 percent / NBS; AIBN / CCl4 / 10 h / Heating
6.1: 99 percent / NaN3 / ethanol; H2O / 8 h / Heating
7.1: NaBH4; [4(S)-Ph-oxazolidin-2-ylidene][4(S)-Ph-2-oxazolin-2-yl](CN)C / CoCl2*6H2O / ethanol; dimethylformamide / 24 h / 25 °C
View Scheme
参考文献
Paraskar, Abhimanyu S.; Sudalai, Arumugam
Tetrahedron, 2006 , vol. 62, # 20 p. 4907 - 4916
反应条件
1: 88 percent / Na2CO3; O2 / Pd(OAc)2 / dimethylformamide / 12 h / 50 °C / 760 Torr
2: 90 percent / NBS; AIBN / CCl4 / 10 h / Heating
3: 99 percent / NaN3 / ethanol; H2O / 8 h / Heating
4: NaBH4; [4(S)-Ph-oxazolidin-2-ylidene][4(S)-Ph-2-oxazolin-2-yl](CN)C / CoCl2*6H2O / ethanol; dimethylformamide / 24 h / 25 °C
View Scheme
参考文献
Paraskar, Abhimanyu S.; Sudalai, Arumugam
Tetrahedron, 2006 , vol. 62, # 20 p. 4907 - 4916
反应条件
sodium hydride in tetrahydrofuran
Heating;
参考文献
Mulzer, Johann; Zuhse, Ralf; Schmiechen, Ralph
Angewandte Chemie, 1992 , vol. 104, # 7 p. 914 - 915
反应条件
1: With dirhodium(II) tetrakis[methyl 4(R)-2-oxazolidinone-4-carboxylate] in dichloromethane
2 h; Heating;
2: With trifluoroacetic acid
T=20°C; 5 h; Title compound not separated from byproducts;
参考文献
Liu, Wei-Jun; Chen, Zhen-Liang; Chen, Zhi-Yong; Hu, Wen-Hao
Tetrahedron Asymmetry, 2005 , vol. 16, # 9 p. 1693 - 1698
反应条件
triethylsilane; boron trifluoride diethyl etherate; ammonia; titanium tetrachloride; lithium
Yield given. Multistep reaction;
参考文献
Meyers, A. I.; Snyder, Lawrence
Journal of Organic Chemistry, 1993 , vol. 58, # 1 p. 36 - 42
