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; T. Patrick Montgomery; Michael J. Krische

doi:10.1039/C2CC31743E

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Chemical Communications

Issue 39, 2012

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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

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

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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

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

DOI: 10.1039/C2CC31743E
Received 08 Mar 2012, Accepted 09 Mar 2012
First published online 04 Apr 2012

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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.

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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

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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

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