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Enantioselective Conjugate Additions of 2-Alkoxycarbonyl-3(2 H)-furanones
Petra Vojáčková1,2, David Chalupa1,2, Jozef Prieboj1
1Department of Chemistry , Masaryk University , Brno , 625 00 , Czech Republic.
Abstract:
Enantioselective conjugate additions of in situ generated 2-alkoxycarbonyl-3(2 H)-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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