Recent Advances in Cycloaddition Reactions of Donor-Acceptor Oxiranes via Carbon-Carbon Bond Cleavage.

Yanqing Zhang,Meng Cheng,Zuliang Chen,Yingjing Wei,Junliang Zhang

Published 2025 in Chemistry - An Asian Journal

ABSTRACT

Oxiranes exhibit two distinct ring-opening modes: cleavage of the C-O bond or cleavage of the C-C bond. Among these, reactions involving C-O bond cleavage have been extensively reviewed. This article provides an overview of the research progress over the past several decades on the cycloaddition reactions of donor-acceptor (D-A) oxiranes via C-C bond cleavage. Under suitable catalytic conditions, D-A oxiranes undergo ring-opening through C-C bond cleavage to form carbonyl ylides, which can participate in [3+n] cycloaddition reactions with aldehydes, imines, alkenes, alkynes, indoles, purines, etc.

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