Asymmetric synthesis of octahydroindoles via a domino robinson annulation/5-endo intramolecular aza-michael reaction

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RECERCAT Principal > Universitat de Barcelona > Farmacologia, Toxicologia i Química Terapèutica > Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) > Visualizar documento

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dc.contributor	Universitat de Barcelona
dc.contributor.author	Parra Montes, Claudio
dc.contributor.author	Bosch, Caroline
dc.contributor.author	Gómez-Bengoa, Enrique
dc.contributor.author	Bonjoch i Sesé, Josep
dc.contributor.author	Bradshaw, Ben
dc.date	2017-07-19T15:13:44Z
dc.date	2016-09-08
dc.date	2017-07-19T15:13:44Z
dc.date	info:eu-repo/date/embargoEnd/2017-09-08
dc.identifier.citation	0022-3263
dc.identifier.citation	666642
dc.identifier.uri	http://hdl.handle.net/2445/114102
dc.format	8 p.
dc.format	application/pdf
dc.language.iso	eng
dc.publisher	American Chemical Society
dc.relation	Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.6b01568
dc.relation	Journal of Organic Chemistry, 2016, vol. 81, p. 10172-10179
dc.relation	https://doi.org/10.1021/acs.joc.6b01568
dc.rights	(c) American Chemical Society , 2016
dc.rights	info:eu-repo/semantics/embargoedAccess
dc.subject	Química orgànica
dc.subject	Síntesi orgànica
dc.subject	Alcaloides
dc.subject	Organic chemistry
dc.subject	Organic synthesis
dc.subject	Alkaloids
dc.title	Asymmetric synthesis of octahydroindoles via a domino robinson annulation/5-endo intramolecular aza-michael reaction
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/acceptedVersion
dc.description.abstract	A straightforward two-step asymmetric synthesis of octahydroindoles has been developed based on two complimentary strategies: (i) an organocatalyzed Michael reaction followed by a tandem Robinson-aza-Michael double cyclization catalyzed by PS-BEMP; (ii) a diastereoselective cyclization, which formally constitutes a remote 1,6 asymmetric induction mediated by PS-BEMP. This allowed the construction of complex octahydroindoles with up to 4 stereocenters, excellent enantioselectivities (up to 95% ee) and complete diastereoselective control in a single pot operation. DFT calculations were performed to understand the origin of this effect.

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