Title:
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Asymmetric synthesis of octahydroindoles via a domino robinson annulation/5-endo intramolecular aza-michael reaction
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Author:
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Parra Montes, Claudio; Bosch, Caroline; Gómez-Bengoa, Enrique; Bonjoch i Sesé, Josep; Bradshaw, Ben
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Other authors:
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Universitat de Barcelona |
Abstract:
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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(s):
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-Química orgànica -Síntesi orgànica -Alcaloides -Organic chemistry -Organic synthesis -Alkaloids |
Rights:
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(c) American Chemical Society , 2016
info:eu-repo/semantics/embargoedAccess |
Document type:
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Article Article - Accepted version |
Published by:
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American Chemical Society
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