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

Enrique Gómez-Bengoa; Aitor Landa; Aitziber Lizarraga; Antonia Mielgo; Mikel Oiarbide; Claudio Palomo

doi:10.1039/C0SC00402B

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Catalytic asymmetric α-alkylation of aldehydesvia a S_N2′-type addition-elimination pathway†

Enrique Gómez-Bengoa,^a Aitor Landa,^a Aitziber Lizarraga,^a Antonia Mielgo,^a Mikel Oiarbide^a and Claudio Palomo*^a

Author affiliations

* Corresponding authors

^a Departamento de Química Orgánica I, Universidad del País Vasco, Apdo. 1072, San Sebastián, Spain
E-mail: claudio.palomo@ehu.es
Fax: (+) 943015270

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 S_N2′-type addition-elimination pathway involving ammonium salt intermediates, are provided.

Download options Please wait...

Supplementary files

Experimental procedures, spectral data for all new compounds, stereochemical proofs, and detailed computational data PDF (5946K)

Article information

DOI: https://doi.org/10.1039/C0SC00402B
Article type: Edge Article
Submitted: 30 Jul 2010
Accepted: 22 Sep 2010
First published: 25 Oct 2010

Download Citation

Chem. Sci., 2011,2, 353-357

Permissions

Request permissions

Catalytic asymmetric α-alkylation of aldehydesvia a S_N2′-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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Science