Enantioselective Conjugate Additions of 2-Alkoxycarbonyl-3(2H)-furanones
Result 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.
Keywords
3(2h)-furanonesproductcyclizationrocaglamideadjacent quaternaryasymmetric-synthesis1,3-dicarbonyl compounds2-substituted benzofuran-3(2h)-onesmichael additionsbeta-keto-esters
The result's identifiers
Result code in IS VaVaI
Alternative codes found
RIV/00216224:14310/18:00105487
Result on the web
DOI - Digital Object Identifier
Alternative languages
Result language
angličtina
Original language name
Enantioselective Conjugate Additions of 2-Alkoxycarbonyl-3(2H)-furanones
Original language 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.
Czech name
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Czech description
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Classification
Type
Jimp - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic Letters
ISSN
1523-7060
e-ISSN
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Volume of the periodical
20
Issue of the periodical within the volume
22
Country of publishing house
US - UNITED STATES
Number of pages
5
Pages from-to
7085-7089
UT code for WoS article
000451101500024
EID of the result in the Scopus database
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Basic information
Result type
Jimp - Article in a specialist periodical, which is included in the Web of Science database
OECD FORD
Organic chemistry
Year of implementation
2018