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Title: Asymmetric synthesis of octahydroindoles via a domino robinson annulation/5-endo intramolecular aza-michael reaction
Author: Parra Montes, Claudio
Bosch, Caroline
Gómez-Bengoa, Enrique
Bonjoch i Sesé, Josep
Bradshaw, Ben
Keywords: Química orgànica
Síntesi orgànica
Organic chemistry
Organic synthesis
Issue Date: 8-Sep-2016
Publisher: American Chemical Society
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.
Note: Versió postprint del document publicat a:
It is part of: Journal of Organic Chemistry, 2016, vol. 81, p. 10172-10179
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ISSN: 0022-3263
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

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