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Homoallylic Alcohols via a Chemo‐Enzymatic One‐Pot Oxidation–Allylation Cascade
Author(s) -
Fuchs Michael,
Schober Markus,
Pfeffer Jan,
Kroutil Wolfgang,
BirnerGruenberger Ruth,
Faber Kurt
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100380
Subject(s) - chemistry , yield (engineering) , pinacol , galactose oxidase , organic chemistry , bromide , alcohol , allyl bromide , enzyme , alcohol oxidase , catalysis , biochemistry , pichia pastoris , materials science , metallurgy , gene , recombinant dna
Abstract 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.