Enantioselective Synthesis of Acyclic Orthogonally Functionalized Compounds Bearing a Quaternary Stereocenter Using Chiral Ammonium Salt Catalysis. Issue 8 (5th August 2021)

• Record Type: Journal Article
• Authors: Röser, Katharina; Berger, Bettina; Widhalm, Michael; Waser, Mario
• Is Part Of: ChemistryOpen. Volume 10:Issue 8(2021)
• Page Start: 756
• Page End: 759
• Publication Date: 2021-08-05
• Subjects: ammonium salt catalysis -- asymmetric alkylation reactions -- cyanoacetates -- phase-transfer catalysis -- quaternary stereogenic centers; Chemistry -- Periodicals; 540; 540.5
• DOI: 10.1002/open.202100162
• Languages: English
• ISSNs: 2191-1363

Abstract

Abstract: We herein report an asymmetric protocol to access a series of orthogonally functionalized acyclic chiral target molecules containing a quaternary stereogenic center by carrying out the enantioselective α‐alkylation of novel orthogonally functionalized dioxolane‐containing cyanoacetates under chiral ammonium salt catalysis. By using just 1 mol % of Maruoka's spirocyclic ammonium salt catalysts enantioselectivities up to e.r.=97.5 : 2.5 could be achieved and further functional group manipulations of the products were carried out as well. Abstract : Highly functionalized acyclic compounds bearing a quaternary stereocenter can be accessed by using a chiral ammonium salt‐catalyzed α‐alkylation protocol.