Chemical and Pharmaceutical Bulletin p. 114 - 119 (2000)
Update date:2022-07-30
Topics:
Kawase, Masami
Hirabayashi, Michitaka
Kumakura, Hiroko
Saito, Setsuo
Yamamoto, Katsumi
The Dakin-West reaction of N-alkoxycarbonyl-N-alkyl-α-amino acids (1a - j) with trifluoroacetic anhydride in the presence of pyridine gave α-amido trifluoromethyl ketones (2a - j), in which probable intermediates were mesoionic 1,3-oxazolium-5-olates (munchnones). The diastereoselective reduction of 2a - f with NaBH4 gave the threo-aminoalcohols (5a - f), which may be explained by the Felkin-Anh model. This was confirmed by converting 5a - f into trans-5-trifluoromethyl-2-oxazolidinones (6a - f) in good yields.
View MoreShandong Xingshun New Material Co., Ltd.
website:http://www.sd-xingshun.com
Contact:+86-519-86461196/+86-519-86464994
Address:Middle of Luhua East Road, Dingtao District
VanderArk International Limited
Contact:86-10-82437576
Address:Qing He
Suzhou Jingye Medicine & Chemical Co., Ltd
website:http://www.jingyechem.cn
Contact:+86-512-66658588
Address:No. 88, Sanlian Street, Jinfeng Road, Suzhou New District, Jiangsu Province, P. R. China
Contact:86-574-26865651
Address:529 YuanBaoShan Road, Beilun District
Wuhan Benjamin Pharmaceutical Chemical Co.,Ltd
Contact:86-27-52341789
Address:Room 1518 B suite, optical valley time square, No 111 Guanshan Road, Hongshan District,Wuhan,Hubei Province,China.
Doi:10.1016/S0020-1693(99)00477-6
(2000)Doi:10.1016/S0040-4039(97)01770-X
(1997)Doi:10.1002/poc.1086
(2006)Doi:10.1007/s11172-009-0167-3
(2009)Doi:10.1016/j.jorganchem.2012.10.038
(2013)Doi:10.1021/jo001136i
(2001)
