Sustainable gold catalysis: synthesis of new spiroacetals

Various [O,O]- and [N,O]-spiroacetals were synthesized by gold-catalyzed spirocyclization of suitable functionalized alkynes. Whereas simple spiroacetals with two heteroatoms were readily obtained by regioselective cyclization of acetylenic diols or aminoalcohols, hitherto unknown spirocyclic isoxaz...

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Bibliographic Details
Published inPure and applied chemistry Vol. 88; no. 4; pp. 391 - 399
Main Authors Wagner, Bernd, Belger, Katrin, Minkler, Stefan, Belting, Volker, Krause, Norbert
Format Journal Article
LanguageEnglish
Published Berlin De Gruyter 01.04.2016
Walter de Gruyter GmbH
Subjects
Aldehydes
Alkynes
Catalysis
Chemical synthesis
Diols
ESOC-19
Gold
gold catalysis
Green Chemistry
Hydrazines
Isoxazolidines
multicomponent reactions
spiroacetals
Sustainability
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Summary:Various [O,O]- and [N,O]-spiroacetals were synthesized by gold-catalyzed spirocyclization of suitable functionalized alkynes. Whereas simple spiroacetals with two heteroatoms were readily obtained by regioselective cyclization of acetylenic diols or aminoalcohols, hitherto unknown spirocyclic isoxazolidines and pyrazolidines bearing three heteroatoms were formed by three-component coupling of alkynols, aldehydes, and protected hydroxylamine or hydrazine derivatives. The sustainability of these spirocyclizations was improved by using recyclable gold catalysts in water or nanomicelles as reaction medium.
ISSN:0033-4545
1365-3075
DOI:10.1515/pac-2016-0406