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Asymmetric synthesis of octahydroindoles via a domino robinson annulation/5-endo intramolecular aza-michael reaction
Parra Montes, Claudio; Bosch, Caroline; Gómez-Bengoa, Enrique; Bonjoch i Sesé, Josep; Bradshaw, Ben
Universitat de Barcelona
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.
Química orgànica
Síntesi orgànica
Alcaloides
Organic chemistry
Organic synthesis
Alkaloids
(c) American Chemical Society , 2016
info:eu-repo/semantics/embargoedAccess
Artículo
info:eu-repo/semantics/acceptedVersion
American Chemical Society
         

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