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ID 57800
Title Alternative
Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts
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Author
Kidou, Chihiro Graduate School of Natural Science and Technology, Okayama University
Mizoguchi , Haruki Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID
Nehira, Tatsuo Graduate School of Integrated Sciences for Life, Hiroshima University
Sakakura, Akira Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID publons researchmap
Abstract
Organoammonium salts of dipeptide-derived chiral tri-amines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of alpha-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although alpha-(p-methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, alpha-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.
Keywords
acyloxyacroleins
1,3-dipolar cycloaddition
isoxazolidines
nitrones
organocatalysis
asymmetric catalysis
Note
This is an Accepted Manuscript of an article published by Georg Thieme Verlag in Synlett 2019; 30(15): 1835-1839 "Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts
Published Date
2019-09-17
Publication Title
Synlett
Volume
volume30
Issue
issue15
Publisher
Georg Thieme Verlag
Start Page
1835
End Page
1839
ISSN
0936-5214
NCID
AA10731110
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
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author
DOI
Web of Science KeyUT
Related Url
isVersionOf https://doi.org/10.1055/s-0039-1690133