Rhodium/diene-catalyzed asymmetric arylation of N-Boc-protected α,β-unsaturated δ-lactam with arylboronic acids: enantioselective synthesis of 4-aryl-2-piperidinones

Autor:	Chen-Guo Feng, Hong-Jie Yu, Ping Tian, Cai-Yun Sun, Ya-Bing Wei, Guo-Qiang Lin, Zhi-Tao He
Rok vydání:	2012
Předmět:	Diene Aryl Organic Chemistry Enantioselective synthesis chemistry.chemical_element Biochemistry Medicinal chemistry Toluene Catalysis Rhodium Adduct chemistry.chemical_compound chemistry Drug Discovery Lactam
Zdroj:	Tetrahedron. 68:9186-9191
ISSN:	0040-4020
DOI:	10.1016/j.tet.2012.09.001
Popis:	Utilizing toluene/isopropanol (20:1 to 40:1) as a solvent and KHF2 as an additive, the rhodium/diene-catalyzed asymmetric arylation (RCAA) reaction of arylboronic acids to N-Boc-protected α,β-unsaturated δ-lactam proceeded smoothly to afford chiral 4-aryl-2-piperidinones with high to excellent yields (up to 94%) and enantioselectivities (up to >99% ee). Further conversion of adduct (R)-1-(tert-butyloxycarbonyl)-4-(4-chlorophenyl)-2-piperidone to (R)-Homobaclofen hydrochloride was also presented.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a0ff6477f54d690a7f635c38cab6c96a https://doi.org/10.1016/j.tet.2012.09.001 Zobrazit plný text záznamu Full Text from ScienceDirect