Journal
ACS CATALYSIS
Volume 7, Issue 4, Pages 2397-2402Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b03651
Keywords
gold catalysis; enantioselective synthesis; tetrahydropyrans; N-heterocyclic carbenes; allenamide; cycloaddition
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Funding
- Spanish MINECO [SAF2013-41943-R, CTQ2013-48164-C2-1-P, CTQ2013-48164-C2-2-P]
- Conselleria de Cultura, Educacion e Ordenacion Universitaria [GRC2013-041, 2015-CP082]
- Centro Singular de Investigacion de Galicia accreditation [ED431G/09]
- European Regional Development Fund (ERDF)
- European Research Council [340055]
- Junta de Andalucia [2012/FQM 1078]
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A straightforward and atom-economical enantio-selective approach to highly substituted tetrahydropyrans is reported. The process, which consists of an intermolecular gold-catalyzed [2+2+2] cycloaddition between allenamides, alkenes, and aldehydes, is efficiently catalyzed by both phosphoramidite- and chiral N-heterocyclic carbene-gold catalysts, occurs with complete chemoselectivity and regioselectivity, moderate diastereoselectivity, and moderate to very good enantioselectivities.
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