(1R,2S,5R)-(-)-薄荷基(S)-对甲苯亚磺酸酯合成路线 （共 50 条）
反应条件
1.1: LiN(Me3Si)2 / tetrahydrofuran / -70 °C 1.2: NH4Cl / tetrahydrofuran; H2O 2.1: 92 percent / DEAD / tetrahydrofuran / 0.67 h / 0 - 25 °C 3.1: benzene / 1.5 h / 40 °C 4.1: tetrahydrofuran / 0.25 h / -70 °C 5.1: 80 percent / TFA / CH2Cl2 / 1 h / 0 - 25 °C View Scheme
参考文献
Asensio, Amparo; Bravo, Pierfrancesco; Crucianelli, Marcello; Farina, Alessandra; Fustero, Santos; Soler, Juan Garcia; Meille, Stefano V.; Panzeri, Walter; Viani, Fiorenza; Volonterio, Alessandro; Zanda, Matteo
European Journal of Organic Chemistry, 2001 , # 8 p. 1449 - 1458
反应条件
in diethyl ether; benzene T=0 - 20°C;
参考文献
Bode, Moira L.; Gates, Paul J.; Gebretnsae, Samson Y.; Vleggaar, Robert
Tetrahedron, 2010 , vol. 66, # 11 p. 2026 - 2036
反应条件
in toluene T=-60 - -20°C;
参考文献
Satoh, Tsuyoshi; Oohara, Teruhiko; Ueda, Yoshiko; Yamakawa, Koji
Journal of Organic Chemistry, 1989 , vol. 54, # 13 p. 3130 - 3136
反应条件
1.1: LiHMDS / tetrahydrofuran / 1.5 h / 20 °C 1.2: tetrahydrofuran / 2 h / -78 - 20 °C 1.3: 61 percent / LiHMDS / tetrahydrofuran / 0.67 h / -78 - -45 °C 2.1: 97 percent / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C View Scheme
参考文献
Davis, Franklin A.; Liu, Hu; Zhou, Ping; Fang, Tianan; Reddy, G. Venkat; Zhang, Yulian
Journal of Organic Chemistry, 1999 , vol. 64, # 20 p. 7559 - 7567
反应条件
magnesium 1.) ether, 2.) benzene, room temp., 2 h; Yield given. Multistep reaction;
参考文献
Solladie, Guy; Hutt, Jean; Girardin, Andre
Synthesis, 1987 , # 2 p. 173
反应条件
n-butyllithium 1.) THF, hexane, -78 deg C,15 min, 2.) THF, hexane, RT, 1.3 h; Yield given. Multistep reaction;
参考文献
Garcia-Ruano, Jose L.; Alonso, Raquel; Zarzuelo, Maria M.; Noheda, Pedro
Tetrahedron: Asymmetry, 1995 , vol. 6, # 5 p. 1133 - 1142
反应条件
tert.-butyl lithium; sodium hydride in tetrahydrofuran; pentane T=0°C; 0.666667 h;
参考文献
Solladie; Bauder; Rossi
Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 7774 - 7777
反应条件
1: 72 percent / diethyl ether / 1 h / 0 °C 2: 38 percent / t-BuLi / tetrahydrofuran / 15 h / -80 °C 3: 21 percent / t-BuLi / tetrahydrofuran / -85 °C View Scheme
参考文献
Furukawa, Naomichi; Ogawa, Satoshi; Matsumura, Kazunori; Fujihara, Hisashi
Journal of Organic Chemistry, 1991 , vol. 56, # 22 p. 6341 - 6348
反应条件
1: BrFc With n-butyllithium in tetrahydrofuran; hexane T=20°C; 0.333333 h; Inert atmosphere; 2: L-menthyl (S)-p-tolylsulfinate in tetrahydrofuran; hexane T=-78°C; 0.5 h; Inert atmosphere;
参考文献
Musikhina; Utepova; Serebrennikova; Chupakhin; Charushin
Russian Journal of Organic Chemistry, 2013 , vol. 49, # 8 p. 1191 - 1194
Zh. Org. Khim., 2013 , vol. 49, # 8 p. 1207 - 1210,4
反应条件
2: PhSO3H
View Scheme
参考文献
Mikolajczyk,M. et al.
Journal of the Chemical Society, Chemical Communications, 1976 , p. 568 - 569
