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Regio‐ and Enantioselective α,γ‐Dialkylation of α,β‐Unsaturated Aldehydes Through Cascade Organocatalysis
Author(s) -
Kutwal Mahesh S.,
Padmaja Venkata M. D.,
Appayee Chandrakumar
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000245
Subject(s) - enantioselective synthesis , chemistry , organocatalysis , electrophile , organic chemistry , regioselectivity , absolute configuration , derivative (finance) , combinatorial chemistry , stereochemistry , catalysis , financial economics , economics
The first regio‐ and enantioselective organocatalytic cascade α,γ‐dialkylation of α,β‐unsaturated aldehydes is achieved. Substrates scope is demonstrated with a variety of α,β‐unsaturated aldehydes and alkylating agents. The absolute configuration of the α,γ‐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 α,γ‐difunctionalization of α,β‐unsaturated aldehydes using other electrophiles are currently underway in our laboratory.