Catalytic asymmetric α-alkylation of aldehydesvia a S N 2′-type addition-elimination pathway
- 25 October 2010
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 2 (2) , 353-357
Abstract
A novel method for the direct, amine-catalyzed, highly enantioselective α-alkylation of aldehydes is described that is founded upon the use of electrondeficient allylic halides as alkylating agents and DABCO or DMAP as coadyuvant. Both experimental observations and DFT calculations, in support of a SN2′-type addition-elimination pathway involving ammonium salt intermediates, are provided.Keywords
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