Journal of Organic Chemistry p. 1057 - 1074 (2016)
Update date:2022-08-15
Topics:
Szczes?niak, Piotr
Pieczykolan, Micha?
Stecko, Sebastian
An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.
View MoreSuzhou Tianma Specialty Chemicals Co.,Ltd
Contact:+86-512-68090577
Address:#199, Huayuan Rd, Mudu, Suzhou, Jiangsu, CHINA
Jiangsu Jiuri Chemical Co.,Ltd.
Contact:+86-519-82118868
Address:Tianwang Town, Jurong City, Jiangsu Province, China
Jiangsu Chiatai Qingjiang Pharmaceutical Co.,Ltd
Contact:+86-517-86283327
Address:9 North Hantai Road, Huaian, China
Ningbo Hi-tech Zone Nice-Synth Chemical Industry Ltd.
Contact:+86-(574)-81110986
Address:No. 1210, Building 3, Wante Business Centre, Hi-tech Zone, Ningbo
Contact:+86 512 6287 2180
Address:398 Ruoshui Road, Suzhou Industrial Park, Suzhou, Jiangsu, P. R. China
Doi:10.1007/s11164-012-0601-2
(2013)Doi:10.1021/acs.orglett.8b03356
(2018)Doi:10.1016/S0040-4020(98)00500-6
(1998)Doi:10.1016/j.tetlet.2012.05.085
(2012)Doi:10.1002/anie.201806059
(2018)Doi:10.1016/j.tetasy.2016.10.008
(2016)