Homoallylic Alcohols via a Chemo-Enzymatic One-Pot Oxidation-Allylation Cascade

• Published in: Advanced synthesis & catalysis Vol. 353; no. 13; pp. 2354 - 2358
• Main Authors: Fuchs, Michael, Schober, Markus, Pfeffer, Jan, Kroutil, Wolfgang, Birner-Gruenberger, Ruth, Faber, Kurt
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2011; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Alcohols; B derivatives; Barbier-type coupling; biocatalysis; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; boronic acids; cascade reaction; Chemistry; Elongation; Esters; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; Fusarium; Galactose; galactose oxidase; indium; Joining; Methods. Procedures. Technologies; Organic chemistry; Organometalloidal and organometallic compounds; Oxidase; Preparations and properties; Transformations; One pot reaction; Biocatalysis; Enzyme; Chemoselectivity; cascade reaction; Barbier-type coupling; Alcohol; Indium; Allylation; Enzymatic method; Galactose oxidase; Boron Organic compounds; Oxidation; Oxidoreductases; Boronic acids; Homoallylic compound; Successive reaction
• ISSN: 1615-4150; 1615-4169; 1615-4169
• DOI: 10.1002/adsc.201100380

A chemo‐enzymatic one‐pot, two‐step transformation of (hetero)‐benzylic and cinnamic alcohols to yield the elongated homoallylic sec‐alcohols in water in up to 96% isolated yield has been developed. The sequence comprised an enzymatic alcohol oxidation using galactose oxidase from Fusarium sp. NRRL 2903 to furnish the corresponding aldehydes, which were subjected directly to allylation via indium(0)‐mediated Barbier‐type coupling with allyl bromide or by addition of allylboronic acid pinacol ester.