Enantioselective Conjugate Additions of 2-Alkoxycarbonyl-3(2H)-furanonesClick to copy article linkArticle link copied!
- Petra VojáčkováPetra VojáčkováDepartment of Chemistry, Masaryk University, Brno, 625 00, Czech RepublicInternational Clinical Research Center, St. Anne’s University Hospital, Brno, 656 91, Czech RepublicMore by Petra Vojáčková
- David ChalupaDavid ChalupaDepartment of Chemistry, Masaryk University, Brno, 625 00, Czech RepublicInternational Clinical Research Center, St. Anne’s University Hospital, Brno, 656 91, Czech RepublicMore by David Chalupa
- Jozef PriebojJozef PriebojDepartment of Chemistry, Masaryk University, Brno, 625 00, Czech RepublicMore by Jozef Prieboj
- Marek NečasMarek NečasDepartment of Chemistry, Masaryk University, Brno, 625 00, Czech RepublicMore by Marek Nečas
- Jakub Švenda*Jakub Švenda*E-mail: [email protected]Department of Chemistry, Masaryk University, Brno, 625 00, Czech RepublicInternational Clinical Research Center, St. Anne’s University Hospital, Brno, 656 91, Czech RepublicMore by Jakub Švenda
Abstract

Enantioselective conjugate additions of in situ generated 2-alkoxycarbonyl-3(2H)-furanones to three distinct types of π-electrophiles (terminal alkynones, α-bromo enones, and α-benzyl nitroalkenes) are reported. Catalysis by a nickel(II)–diamine complex provided alkynone-derived adducts with high enantioselectivity, preferentially as the Z-isomers, and completely suppressed the undesired O-alkylation pathway. A cupreidine-based catalyst enabled extension of the enantioselective conjugate additions to α-bromo enones and α-benzyl nitroalkenes. The densely functionalized adducts that result are useful precursors to synthetic analogs of spirocyclic natural products pseurotins.
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