Asymmetric Allylic Amination of Morita–Baylis–Hillman Carbonates with Silylated tert‐Butylhydroxycarbamate Derivatives. Issue 14 (13th April 2017)

• Record Type: Journal Article
• Authors: Kamlar, Martin; Císařová, Ivana; Hybelbauerová, Simona; Veselý, Jan
• Is Part Of: European journal of organic chemistry. Issue 14(2017)
• Page Start: 1926
• Page End: 1930
• Publication Date: 2017-04-13
• Subjects: Alkaloids -- Allylic compounds -- Amination -- Asymmetric synthesis -- Organocatalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700222
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert ‐butylhydroxycarbamates using β‐isocupreidine as an organocatalyst was investigated. The corresponding products were obtained in good yields with high enantioselectivities. The scope and limitations of the reported protocol were explored, and representative transformations of the adducts toward heterocyclic compounds were highlighted. Abstract : The enantioselective amination of Morita–Baylis–Hillman carbonates with silylated derivatives of tert ‐butylhydroxycarbamates by using β‐isocupreidine (β‐ICD) as an organocatalyst is described. The scope and limitations of the reported protocol are outlined, and representative transformations of the adducts toward heterocyclic compounds are highlighted.