(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
n-butyllithium 1) THF, hexane, -50 deg C, 5 min, rt, 1 h; 2) THF, hexane, -20 deg C, 10 min, rt, 1 h; 3) THF, hexane, reflux, 8 h; Yield givenMultistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
参考文献
Mikolajczyk, Marian; Perlikowska, Wieslawa; Omelanczuk, Jan; Cristau, Henri-Jean; Perraud-Darcy, Anne
Journal of Organic Chemistry, 1998 , vol. 63, # 26 p. 9716 - 9722
反应条件
lithium hexamethyldisilazane in tetrahydrofuran T=-78 - 20°C; Substitution; 1 h;
参考文献
Davis; Zhang; Andemichael; Fang; Fanelli
Journal of Organic Chemistry, 1999 , vol. 64, # 4 p. 1403 - 1406
反应条件
1: With lithium hexamethyldisilazane in tetrahydrofuran T=-70°C; 2: With ammonium chloride in tetrahydrofuran; water
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 tetrahydrofuran T=-78 - 20°C; 5 h; Yield given. Yields of byproduct given;
参考文献
Davis, Franklin A.; Reddy, Rajarathnam E.; Szewczyk, Joanna M.; Reddy, G. Venkat; Portonovo, Padma S.; Zhang, Huiming; Fanelli, Dean; Reddy, R. Thimma; Zhou, Ping; Carroll, Patrick J.
Journal of Organic Chemistry, 1997 , vol. 62, # 8 p. 2555 - 2563
反应条件
1: 1-bromo-2-methyl benzene With magnesium in diethyl ether 2: (SS)-(-)-L-Menthyl toluene-p-sulfinate in tetrahydrofuran; diethyl ether T=-78°C; 3 h; Further stages.;
参考文献
Garcia Ruano, Jose L.; Aleman, Jose; Soriano, Jose F.
Organic Letters, 2003 , vol. 5, # 5 p. 677 - 680
参考文献
Andersen,K.K. et al.
Journal of the American Chemical Society, 1964 , vol. 86, p. 5637 - 5646
反应条件
1: (SS)-(-)-L-Menthyl toluene-p-sulfinate With lithium hexamethyldisilazane in tetrahydrofuran T=-78 - 20°C; 5 h; Inert atmosphere; 2: benzaldehyde in tetrahydrofuran T=-78°C; 2 h; Inert atmosphere;
参考文献
Blangetti, Marco; Croce, Gianluca; Deagostino, Annamaria; Mussano, Eleonora; Prandi, Cristina; Venturello, Paolo
Journal of Organic Chemistry, 2011 , vol. 76, # 6 p. 1814 - 1820
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
1: 99 percent / toluene / -60 - -20 °C 2: K2CO3, N-chlorosuccinimide (NCS) / CH2Cl2 / 20 h / Ambient temperature View Scheme
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: EtMgI; (SS)-(-)-L-Menthyl toluene-p-sulfinate 2: With N-chloro-succinimide; potassium carbonate
参考文献
Miura, Motofumi; Toriyama, Masaharu; Motohashi, Shigeyasu
Synthetic Communications, 2006 , vol. 36, # 3 p. 259 - 264
