An asymmetric synthesis of (2S,5S)-5-substituted azepane-2-carboxylate derivatives

Autor:	Hardwin O'dowd, Katherine E. Brighty, Michael W. Fichtner, Donn G. Wishka, Goss S. Kauffman, Mark C. Noe, Marion Bédard, Jason G. Lewis, Richard A. Buzon, Brian Samas, Jaap Kooistra, Ivan J. Samardjiev, Kathleen A. Farley, Geeta Yalamanchi
Rok vydání:	2011
Předmět:	Bicyclic molecule Drug discovery Organic Chemistry Enantioselective synthesis Nonene Carboxylic Acids Ketones Bridged Bicyclo Compounds Heterocyclic Chemical synthesis Combinatorial chemistry chemistry.chemical_compound chemistry Azepane Drug Discovery Stereoselectivity Carboxylate
Zdroj:	The Journal of organic chemistry. 76(6)
ISSN:	1520-6904
Popis:	To facilitate a drug discovery project, we needed to develop a robust asymmetric synthesis of (2S,5S)-5-substituted-azepane-2-carboxylate derivatives. Two key requirements for the synthesis were flexibility for elaboration at C5 and suitability for large scale preparation. To this end we have successfully developed a scalable asymmetric synthesis of these derivatives that starts with known hydroxy-ketone 8. The key step features an oxidative cleavage of aza-bicyclo[3.2.2]nonene 14, which simultaneously generates the C2 and C5 substituents in a stereoselective manner.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a0679bee29b243873ab7356ff8fde330 https://pubmed.ncbi.nlm.nih.gov/21275376 Zobrazit plný text záznamu