AI Article Synopsis
- * These innovative methods utilize a redox process, allowing for the production of organometallic nucleophiles without needing traditional reagents like carbonyl additives or chiral auxiliaries.
- * The approach allows selective dehydrogenation of primary alcohols when secondary alcohols are present, facilitating carbon-carbon coupling without the need for protecting groups.
Article Abstract
Catalytic enantioselective hydrogen autotransfer reactions for the direct conversion of lower alcohols to higher alcohols are catalogued and their application to the total synthesis of polyketide natural products is described. These methods exploit a redox process in which alcohol oxidation is balanced by reductive generation of organometallic nucleophiles from unsaturated hydrocarbon pronucleophiles. Unlike classical carbonyl additions, premetalated reagents, chiral auxiliaries and discrete alcohol-to-aldehyde redox reactions are not required. Additionally, chemoselective dehydrogenation of primary alcohols in the presence of secondary alcohols enables C-C coupling in the absence of protecting groups.
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| http://dx.doi.org/10.1021/acs.chemrev.4c00858 | DOI Listing |
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