Multiselective Diels–Alder Reaction of α‑Arylacroleins Catalyzed by Boron Tribromide-Assisted Chiral Phosphoric Acids

A multiselective Diels–Alder (DA) reaction of α-arylacroleins with cyclopentadiene using BBr3-assisted chiral BINOL-derived phosphoric acid catalysts has been developed. This unusual exo- and enantioselective DA reaction can be multicontrolled by the chiral cavity of the in situ-formed acid–base coo...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 35; pp. 6483 - 6488
Main Authors Matsui, Kai, Toh, Kohei, Hatano, Manabu, Ishihara, Kazuaki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.09.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SALT
CYCLOADDITION
LEWIS-ACID
EXO
BRONSTED ACIDS
EQUIVALENT
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Summary:A multiselective Diels–Alder (DA) reaction of α-arylacroleins with cyclopentadiene using BBr3-assisted chiral BINOL-derived phosphoric acid catalysts has been developed. This unusual exo- and enantioselective DA reaction can be multicontrolled by the chiral cavity of the in situ-formed acid–base cooperative catalysts, in particular, suppressing the competitive hetero Diels–Alder (HDA) reaction effectively.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02747