Recueil des Travaux Chimiques des Pays-Bas p. 365 - 368 (1994)
Update date:2022-08-03
Topics:
Poelert, Martin A.
Hulshof, L. A.
Kellogg, Richard M.
Dialkylcarbodiimides in the presence of a Cu(I) catalyst react cleanly with the hydroxyl group of N-methylated (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine.These adducts react with nucleophiles like alkyl and aryl thiols as well as thioic acids and phthalimide to form the substitution products with overall retention of configuration.It is postulated that intramolecular paricipation of the amino group via an SN2 reaction leads to aziridium salts, which are subsequently opened by the nucleophiles via a second SN2 reaction.This synthetic approach is also useful for the inversion of simple secondary alcohols; on treatment with dicyclohexylcarbodiimide followed by benzothioic acid and treatment with LiAlH4, menthol was converted in good yield to neomenthane thiol.
View Morewebsite:http://www.fwdchem.com
Contact:86-21-54450828
Address:Room 802,Lotus Tower ,159 Tianzhou Road,Xuhui District,Shanghai
Shanghai Sungo Technology Chemical Co., Ltd
Contact:0086-21-51385579
Address:Room2010, F/20, Tonghua Plaza, NO 345 Jinxiang Road, Jinqiao Export Processing Zone, Shanghai, 201206 P.R.CHINA
Contact:+86-513-80923002
Address:Suzhou Road 8,Beixin,Qidong,Jiangsu province,P.R.226221,China
Wuhan Kemi-Works Chemical Co., Ltd
website:http://www.kemiworks.com
Contact:86-27-85736489
Address:Rm. 1503, No. 164, Jianghan North Rd., Wuhan, 430022 China
Changzhou Ansciep Chemical Co.,Ltd.
Contact:+86 519 8630 5871
Address:A-710 Boan International, 8 East Guangdian Road,Wujin,Changzhou
Doi:10.1002/ejoc.201100674
(2011)Doi:10.1016/j.bmcl.2014.02.046
(2014)Doi:10.1021/jm00009a014
(1995)Doi:10.1248/cpb.c15-01016
(2016)Doi:10.1021/acs.orglett.8b02854
(2018)Doi:10.1016/0040-4039(94)80136-3
(1994)