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Issue 2, 2011
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Catalytic asymmetric α-alkylation of aldehydesvia a SN2′-type addition-elimination pathway

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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.

Graphical abstract: Catalytic asymmetric α-alkylation of aldehydesvia a SN2′-type addition-elimination pathway

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Publication details

The article was received on 30 Jul 2010, accepted on 22 Sep 2010 and first published on 25 Oct 2010


Article type: Edge Article
DOI: 10.1039/C0SC00402B
Citation: Chem. Sci., 2011,2, 353-357
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    Catalytic asymmetric α-alkylation of aldehydesvia a SN2′-type addition-elimination pathway

    E. Gómez-Bengoa, A. Landa, A. Lizarraga, A. Mielgo, M. Oiarbide and C. Palomo, Chem. Sci., 2011, 2, 353
    DOI: 10.1039/C0SC00402B

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