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- Title
Secondary Amine Catalysed Diastereoselective Cross Domino Reaction: Simple and Efficient Synthesis of Heteroaryl-Substituted Cyclohexanols.
- Authors
Patel, P. N.; Talati, K. S.; Deshmukh, A. G.; Desai, D. H.; Patel, N. C.
- Abstract
An effective secondary amine catalysed approach to the diastereoselective synthesis substituted cyclohexanols was proposed. A steric hindrance driven diastereoselective cross domino reaction gave manifold heteroaryl substituted cyclohexanols with five asymmetric centres in 92–98% yields. The sequence of inter- and intramolecular domino reactions includes Claisen–Schmidt condensation followed by 1,4-Michael addition of heteroaryl carbaldehydes and heteroaryl acetyl derivatives. HPLC study of the reactions shows outstanding self diastereoselectivity (dr > 99%) in the formation of one set of enantiomers out of sixteen possible enantiomeric pairs. The structures of all the synthesized molecules were confirmed by HRMS, NMR and IR spectroscopy methods.
- Subjects
CYCLOHEXANOLS; SECONDARY amines; NUCLEAR magnetic resonance spectroscopy; STERIC hindrance; ENANTIOMERS; CONDENSATION reactions
- Publication
Russian Journal of General Chemistry, 2022, Vol 92, Issue 4, p694
- ISSN
1070-3632
- Publication type
Article
- DOI
10.1134/S1070363222040107