Journal of the Chemical Society. Perkin transactions I p. 1865 - 1872 (1986)
Update date:2022-08-05
Topics:
Belokon, Yuri N.
Bulychev, Aleksandr G.
Ryzhov, Mikhail G.
Vitt, Sergei V.
Batsanov, Andrei S.
et al.
The glycine fragment in the nickel(II) complex formed from the Schiff base of glycine and (S)-o-<(N-benzylprolyl)amino>benzophenone undergoes base-catalysed Michael addition in methanol in the presence of MeONa to the activated olefins methyl acrylate, acrylonitrile, methyl methacrylate, acrolein, and methyl trans-cinnamate.Complexes of substituted (S)-glutamic acid or its derivatives were formed in good chemical yields with almost complete diastereoselection at the α-carbon atom of the amino acid moiety.Diastereoselection at the β- and γ-atoms was not significant, but the isomeric complexes could be easily separated chromatogrphically.Cleavage of the pure diastereoisomers with aqueous HCl gave, in good yields, optically pure glutamic acids and regenerated the original chiral reagent.The configurations of the amino acid β- and γ-carbon atoms were determined by 1H n. m. r. spectroscopy and crystal structure X-ray analysis of the corresponding original complexes.The addition to acrolein, catalysed by triethylamine in methanol, leads to the 1,4-adduct exclusively.The amino acid thus obtained could be converted into (S)-proline by reduction with NaBH4.
View MoreHangzhou jls Flame Retardants Chemical Co.,Ltd
Contact:+86-571-87250387/87250386
Address:MOGANSHAN RODA 1418# SHANGCHENG INDUSTRIAL PARK
Jining tiansheng chemical co.,ltd.
Contact:+86-537-5158722
Address:ROOM 1011, BLOCK B, CUIDU INTERNATIOAL BUSINESS CENTER, JINING CITY, CHINA
LABTER PARMATECH(BEIJING)CO.,LTD
website:http://www.labter.com.cn/
Contact:+86-10-56330744
Address:NO.19,TIANRONG STREET,DAXING BIOMEDICIAL BASE ,ZHONGGUANCUN SCIENCE AND TECHNOLOGY PARK,BEIJING ,CHINA
Contact:+86-10-67147360/67107388
Address:No.18 Guangming Zhongjie, Chongwen District, Beijing, 100061, China
Puyang Willing Chemicals Co.,Ltd.
Contact:86-393-4840366
Address:Puyang Henan China
Doi:10.1002/cber.19701030506
(1970)Doi:10.1021/ol035918k
(2003)Doi:10.1016/S0040-4039(00)92569-3
(1976)Doi:10.1007/BF00811275
(1986)Doi:10.1021/acs.orglett.5b01123
(2015)Doi:10.1248/cpb.30.1706
(1982)
