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Enantioselective gold-catalyzed intermolecular [2+2] versus [4+2]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects.

ABSTRACT: A highly enantioselective [2+2] versus a [4+2]-cycloaddition of 3-styrylindoles to N-allenamides catalyzed by identical gold(i)/chiral phosphoramidite complexes is presented, which provides facile access to synthetically valuable, optically active substituted cyclobutanes and tetrahydrocarbazoles. The cycloaddition mode unexpectedly depends on the electronic nature of the N-substituent 3-styrylindoles, the origin of which could be well rationalized using DFT calculations and experimental results. To the best of our knowledge, the present work represents the first example of such an impressive substituent effect in tuning the reaction mode with high chemo-, regio- and enantioselectivity in asymmetric gold catalysis.

SUBMITTER: Wang Y

PROVIDER: S-EPMC5949851 | biostudies-other | 2015 Oct

REPOSITORIES: biostudies-other

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Enantioselective gold-catalyzed intermolecular [2+2] versus [4+2]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects.

Wang Yidong Y Zhang Peichao P Liu Yuan Y Xia Fei F Zhang Junliang J

Chemical science 20150623 10

A highly enantioselective [2+2] versus a [4+2]-cycloaddition of 3-styrylindoles to N-allenamides catalyzed by identical gold(i)/chiral phosphoramidite complexes is presented, which provides facile access to synthetically valuable, optically active substituted cyclobutanes and tetrahydrocarbazoles. The cycloaddition mode unexpectedly depends on the electronic nature of the N-substituent 3-styrylindoles, the origin of which could be well rationalized using DFT calculations and ...[more]

PMID: 29861893

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