doi: 10.1002/asia.201900938. Epub 2019 Aug 13.
1 Biofunctional Chemistry Laboratory, Alexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, Kazan, 420008, Russia.
2 Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
3 Arbuzov Institute of Organic and Physical, Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov Street, Kazan, 420088, Russia.
4 NMR Laboratory, Institute of Physics, Kazan Federal University, 18 Kremlyovskaya Street, Kazan, 420008, Russia.
Dilyara R Chulakova et al. Chem Asian J. 2019 .
The chiral substituted 1,5-diazacyclooctane (1,5-DACO) is of considerable importance and has attracted attention from a wide range of fields due to their unique chemical and biological properties. Despite the application potential, further study has not been optimized due to difficulties in their synthetic accessibility. Here, we report that the 1,5-DACO bearing a chiral auxiliary obtained from the formal [4+4] cycloaddition of N-alkyl-α,β-unsaturated imines can be further derivatized by nucleophilic alkylation to give various chiral substituted 1,5-DACO derivatives. The removal of the chiral auxiliary was effectively carried out using hydrogenation over Pearlman's catalyst. This methodology allows the production of a broad range of unprecedented optically active 2,6-dialkyl-1,5-DACO, which could not be accessed by other methods.
Keywords: [4+4] cycloaddition; asymmetric synthesis; chiral amines; diazacyclooctane; saturated heterocycles.
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