Issue 39, 2012
From the journal:

Chemical Communications

Consecutive iridium catalyzed C–C and C–H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C–H (2-fluoro)allylation of primary alcohols†

Abbas Hassan,a   T. Patrick Montgomerya  and  Michael J. Krische*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, USA
E-mail: mkrische@mail.utexas.edu
Fax: +1 613 9418447
Tel: +1 512 2325892

Abstract

Commercially available (2-fluoro)allyl chloride serves as an efficient allyl donor in highly enantioselective iridium catalyzed carbonyl (2-fluoro)allylations from the alcohol or aldehyde oxidation level via transfer hydrogenation. Diastereoselective Crabtree hydrogenation of the resulting homoallylic alcohols provides syn-3-fluoro-1-alcohols.

Graphical abstract: Consecutive iridium catalyzed C–C and C–H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C–H (2-fluoro)allylation of primary alcohols

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Article information

DOI
https://doi.org/10.1039/C2CC31743E
Article type
Communication
Submitted
08 Mar 2012
Accepted
09 Mar 2012
First published
04 Apr 2012

Chem. Commun., 2012,48, 4692-4694

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Consecutive iridium catalyzed C–C and C–H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C–H (2-fluoro)allylation of primary alcohols

A. Hassan, T. P. Montgomery and M. J. Krische, Chem. Commun., 2012, 48, 4692 DOI: 10.1039/C2CC31743E

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