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2016-09-08

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/114102

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

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https://doi.org/10.1021/acs.joc.6b01568

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.

Subject

Química orgànica, Síntesi orgànica, Alcaloides

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Organic chemistry, Organic synthesis, Alkaloids

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

Citation

PARRA MONTES, Claudio, et al. Asymmetric synthesis of octahydroindoles via a domino robinson annulation/5-endo intramolecular aza-michael reaction. Journal of Organic Chemistry. 2016. Vol. 81, num. 10172-10179. ISSN 0022-3263. [consulted: 14 of June of 2026]. Available at: https://hdl.handle.net/2445/114102

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