Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites

In this paper, we present a Lewis-acid-promoted reaction of 2-benzoylbenzaldehyde and trialkenyl phosphites, which resulted in the formation of polycyclic phosphonates. The reaction proceeded via nucleophilic attack of trialkenyl phosphite on the carbonyl carbon of 2-benzoylbenzaldehyde. The subsequ...

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Bibliographic Details
Published in:Heterocyclic Communications 2019-05, Vol.25 (1), p.73-77
Main Authors: Yamana, Kenji, Nakano, Hirofumi
Format: Article
Language:English
Subjects:
Carbonyls
cyclic phosphonate
diels-alder reaction
Diels-Alder reactions
Inorganic salts
intramolecular cycloaddition
isobenzofuran
oxaphosphinane
Phosphonates
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Summary:In this paper, we present a Lewis-acid-promoted reaction of 2-benzoylbenzaldehyde and trialkenyl phosphites, which resulted in the formation of polycyclic phosphonates. The reaction proceeded via nucleophilic attack of trialkenyl phosphite on the carbonyl carbon of 2-benzoylbenzaldehyde. The subsequent intramolecular Diels-Alder reaction led to the formation of the cyclic phosphonate.
ISSN:0793-0283
2191-0197
DOI:10.1515/hc-2019-0011