Abstract
Abstract 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.
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