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https://hdl.handle.net/2445/114102| 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 Alcaloides Organic chemistry Organic synthesis Alkaloids |
| 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: https://doi.org/10.1021/acs.joc.6b01568 |
| It is part of: | Journal of Organic Chemistry, 2016, vol. 81, p. 10172-10179 |
| URI: | https://hdl.handle.net/2445/114102 |
| Related resource: | https://doi.org/10.1021/acs.joc.6b01568 |
| ISSN: | 0022-3263 |
| Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| 666642.pdf | 1.11 MB | Adobe PDF | View/Open |
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