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Synthesis 2012; 44(22): 3534-3542
DOI: 10.1055/s-0032-1316796
DOI: 10.1055/s-0032-1316796
paper
Ligand Control of the Cobalt-Catalysed 1,4-Hydrovinylation Reaction
Further Information
Publication History
Received: 17 September 2012
Accepted: 18 September 2012
Publication Date:
02 October 2012 (online)
Abstract
The application of cobalt catalysts to the hydrovinylation of unsymmetrical alkenes and 1,3-dienes was investigated using modular phosphine-phosphite ligands to evaluate the influence of the ligands on the regioselectivity of the reaction. While a ligand with a TADDOL subunit (SchmalzPhos) gave the best results for the β-4 regioisomer, the corresponding BINOL-derived ligand gave predominantly the β-1 regioisomer. The application of (E)-2-methylpenta-1,3-diene in combination with the (nonracemic) BINOL-derived ligand generated the β-4 regioisomer in excellent yields and very high regioselectivities for a number of terminal alkenes bearing various functional groups. In one case, the enantiomeric excess of a chiral product, i.e. a 3,5-dimethylhexa-1,4-diene derivative, was determined by chiral RP-HPLC to be 78% ee.
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For reviews, see:
For 1,2-hydrovinylations catalysed by Ni, see:
For 1,2-hydrovinylations catalysed by Pd, see:
For 1,2-hydrovinylations catalysed by Co, see:
For 1,2-hydrovinylations catalysed by Pt, see:
For 1,2-hydrovinylations catalysed by Ir, see:
For 1,2-hydrovinylations catalysed by Ru, see:
For Fe-catalysed hydrovinylations, see:
For recent general reviews on Co-catalysed reactions, see:
For Co-catalysed 1,4-hydrovinylations, see:
SchmalzPhos = (3aR,8aR)-6-[3-(diphenylphosphino)bi-phenyl-2-yloxy]-2,2-dimethyl-4,4,8,8-tetraphenyltetra-hydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine. For synthetic applications, see also: