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Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans.

ABSTRACT: A new class of phosphorus-containing 1,3-dipoles can be generated by the multicomponent reaction of aldehydes, acid chlorides and the phosphonite PhP(catechyl). These 1,3-dipoles are formally cyclic tautomers of simple Wittig-type ylides, where the angle strain and moderate nucleophilicity in the catechyl-phosphonite favor their cyclization and also direct 1,3-dipolar cycloaddition to afford single regioisomers of substituted products. Coupling the generation of the dipoles with 1,3-dipolar cycloaddition offers a unique, modular route to furans from combinations of available aldehydes, acid chlorides and alkynes with independent control of all four substituents.

SUBMITTER: Erguven H

PROVIDER: S-EPMC8612406 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans.

Erguven Huseyin H Zhou Cuihan C Arndtsen Bruce A BA

Chemical science 20211027 45

A new class of phosphorus-containing 1,3-dipoles can be generated by the multicomponent reaction of aldehydes, acid chlorides and the phosphonite PhP(catechyl). These 1,3-dipoles are formally cyclic tautomers of simple Wittig-type ylides, where the angle strain and moderate nucleophilicity in the catechyl-phosphonite favor their cyclization and also direct 1,3-dipolar cycloaddition to afford single regioisomers of substituted products. Coupling the generation of the dipoles with 1,3-dipolar cycl ...[more]

PMID: 34909148

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