Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 21, Pages 10172-10179Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01568
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Funding
- MINECO (the Ministry of Economy and Competitiveness of Spain) [CTQ2013-41338-P, CTQ2013-47925_C2]
- European Commission [MCITN-2012-316379]
- CONICYT, Chile
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A straightforward, two-step asymmetric synthesis of octahydroindoles has been developed on the basis of two complementary strategies: (i) an organocatalyzed Michael reaction followed by a tandem Robinson-aza-Michael double cyclization catalyzed by PS-BEMP, and (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 four 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.
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