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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.

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.

SUBMITTER: Hassan A

PROVIDER: S-EPMC3448947 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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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.

Hassan Abbas A Montgomery T Patrick TP Krische Michael J MJ

Chemical communications (Cambridge, England) 20120404 39

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. ...[more]

PMID: 22473044

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