Publication details

Enantioselective Conjugate Additions of 2-Alkoxycarbonyl-3(2H)-furanones

Authors

VOJÁČKOVÁ Petra CHALUPA David PRIEBOJ Jozef NEČAS Marek ŠVENDA Jakub

Year of publication 2018
Type Article in Periodical
Magazine / Source Organic Letters
MU Faculty or unit

Faculty of Science

Citation
Web https://pubs.acs.org/doi/10.1021/acs.orglett.8b03039
Doi http://dx.doi.org/10.1021/acs.orglett.8b03039
Keywords BETA-KETO-ESTERS; MICHAEL ADDITIONS; 2-SUBSTITUTED BENZOFURAN-3(2H)-ONES; 1.3-DICARBONYL COMPOUNDS; ASYMMETRIC-SYNTHESIS; ADJACENT QUATERNARY; ROCAGLAMIDE; CYCLIZATION; PRODUCT; 3(2H)-FURANONES
Description Enantioselective conjugate additions of in situ generated 2-alkoxycarbonyl-3(2H)-furanones to three distinct types of pi-electrophiles (terminal alkynones, alpha-bromo enones, and alpha-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-allcylation pathway. A cupreidine-based catalyst enabled extension of the enantioselective conjugate additions to alpha-bromo enones and alpha-benzyl nitroalkenes. The densely functionalized adducts that result are useful precursors to synthetic analogs of spirocyclic natural products pseurotins.
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