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Facile Access to Optically Active 2,6-Dialkyl-1,5-Diazacyclooctanes
Authors
Bulygina K.
Chulakova D.
+8 more
Kurbangalieva A.
Kuznetsov D.
Latypova L.
Lodochnikova O.
Pradipta A.
Smirnov I.
Tanaka K.
Usachev K.
Publication date
1 January 2019
Publisher
Abstract
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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
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Kazan Federal University Digital Repository
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oai:dspace.kpfu.ru:net/158000
Last time updated on 21/02/2020
National Open Repository Aggregator (NORA)
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oai:rour.neicon.ru:rour/199523
Last time updated on 04/04/2020