Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 18, Pages 2720-2724Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000245
Keywords
Amine catalysis; Dialkylation; Cascade reaction; Enantioselectivity; Regioselectivity
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Funding
- SERB, India [CRG/2018/000575]
- IIT Gandhinagar
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The first regio- and enantioselective organocatalytic cascade alpha,gamma-dialkylation of alpha,beta-unsaturated aldehydes is achieved. Substrates scope is demonstrated with a variety of alpha,beta-unsaturated aldehydes and alkylating agents. The absolute configuration of the alpha,gamma-dialkylated product is confirmed using single-crystal X-ray analysis of its carbamate derivative. The practicality of this methodology is showcased by the gram-scale synthesis. Further application of this methodology for the regio- and enantioselective alpha,gamma-difunctionalization of alpha,beta-unsaturated aldehydes using other electrophiles are currently underway in our laboratory.
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