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Synthesis of 3,5‐Disubstituted 1,2‐Dioxolanes
Author(s) -
Pinet Alexis,
Nguyen Linh T.,
Figadère Bruno,
Ferrié Laurent
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000980
Subject(s) - chemistry , electrophile , ring (chemistry) , singlet oxygen , hydrogen peroxide , combinatorial chemistry , nucleophile , dioxolane , peroxide , organic chemistry , oxygen , catalysis
Endoperoxides are a source of bioactive compounds which drove to some important anti‐malarial drugs such as artemisinin or arterolane. 1,2‐Dioxolanes drew the attention of many scientists, through the isolation of numerous natural products containing this peroxidized ring structure such as the plakinic acid family or the biosynthetic study of prostaglandins. Thus, a considerable work was reported for the synthesis of such endoperoxides, but mainly applied to the synthesis of 3,3',5,5'‐tetrasubstituted 1,2‐dioxolanes. The recent isolation of new natural products containing a 3,5‐disubstituted dioxolane ring brought our attention on how to specifically prepare such structures. Herein, we tentatively summarize exhaustively all the methods reported for the synthesis of 3,5‐disubstituted 1,2‐dioxolanes. Therefore, nucleophilic substitution with hydrogen peroxide or hydroperoxide, use of electrophilic singlet oxygen, use of triplet oxygen in radical reaction and the chemistry of peroxycarbenium ions will be presented for this purpose.