Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 10, Pages 2972-2977Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103366
Keywords
aldehydes; allylation; asymmetric catalysis; co-catalysis; transition metals
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Funding
- Mid Sweden University
- Carl Trygger foundation
- European Union
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The first direct intermolecular regiospecific and highly enantioselective a-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd0 complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecific a-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 e.r.; e.r.=enantiomeric ratio). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals, 2-alkyl-butane-1,4-diols, and amines. The concise co-catalytic asymmetric total syntheses of biologically active natural products (e.g., Arundic acid) are disclosed.
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