Beilstein Journal of Organic Chemistry p. 2853 - 2860 (2018)
Update date:2022-08-05
Topics:
Coutant, Eloi P.
Hervin, Vincent
Gagnot, Glwadys
Ford, Candice
Baatallah, Racha
Janin, Yves L.
We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.
View MoreJiangsu Glory Chemical Co., Ltd.
Contact:+86-571-87896791
Address:Yanhua Chemical Park, Hongze, Huai'an, Jiangsu, China
Jiangxi Dongbang Pharmaceutical Co., Ltd.
Contact:+86-795-4433603, 4433388
Address:Fengxin Industrial Park, Fengxin County, Jiangxi Province, P.R.C
Contact:86-15588110016
Address:LINYI CITY,SHANDONG PROVINCE,CHINA
Shandong Yuanli Science and Technology Co., Ltd.
Contact:86-0536-6777557
Address:Zhuliu Industiral Park,Changle County
Chengdu Green Young Biopharmaceutical INC
Contact:+86-28-85337952
Address:1-B-26,Tianhe Industry Park, No.1480 of Tianfu Road,Chengdu,P.R.China,610000
Doi:10.1021/ol400902d
(2013)Doi:10.1021/ja801018r
(2008)Doi:10.1016/j.bmc.2015.08.001
(2015)Doi:10.1021/jm00196a006
(1979)Doi:10.1016/j.bmcl.2007.09.068
(2008)Doi:10.1021/acs.inorgchem.8b02333
(2018)