Journal of Organic Chemistry p. 4177 - 4183 (1995)
Update date:2022-08-05
Topics:
Mickelson, John W.
Belonga, Kenneth L.
Jacobsen, Jon E.
The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step.The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intermolecular Mitsunobu reaction to set the required stereochemistry.The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6- trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction.These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.
View MoreNINGXIA DARONG CHEMICALS & METALLURGY CO.,LTD.
Contact:86-952-2179751
Address:Darong Road, Dawukou, Shizuishan, Ningxia 753001, China
BrightGene Bio-Medical Technology Co., Ltd.
website:https://en.bright-gene.com/
Contact:+86-512-62551801
Address:Building C25 - C31, No. 218 Xinghu Road, Suzhou Industrial Park, Suzhou, Jiangsu, China.
website:http://www.josunpharma.com
Contact:+86-311-80715268 80766839
Address:No.39, Zhaiying Street, Shijaizhuang,Hebei,China
Contact:0550-7041128 0550-7090578
Address:Wangdian Street,Xinjie Town
Chengdu ZY Biochemical Technology Co., LTD
Contact:0086-28-88680086
Address:170 Qingpu Road, Shouan Town, Pujiang County
Doi:10.1007/BF00630584
(1993)Doi:10.1007/BF00698519
()Doi:10.1016/j.tetlet.2018.11.031
(2018)Doi:10.1021/jo01067a079
(1961)Doi:10.1007/BF00698515
(1995)Doi:10.1021/ja01530a076
(1959)