Asymmetric Conjugate Reduction of α,β‐Unsaturated Ketones and Esters with Chiral Rhodium(2,6‐bisoxazolinylphenyl) Catalysts
- 9 December 2005
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 12 (1) , 63-71
- https://doi.org/10.1002/chem.200500841
Abstract
New asymmetric conjugate reduction of β,β‐disubstituted α,β‐unsaturated ketones and esters was accomplished with alkoxylhydrosilanes in the presence of chiral rhodium(2,6‐bisoxazolinylphenyl) complexes in high yields and high enantioselectivity. (E)‐4‐Phenyl‐3‐penten‐2‐one and (E)‐4‐phenyl‐4‐isopropyl‐3‐penten‐2‐one were readily reduced at 60 °C in 95 % ee and 98 % ee, respectively, by 1 mol % of catalyst loading. (EtO)2MeSiH proved to be the best hydrogen donor of choice. tert‐Butyl (E)‐β‐methylcinnamate and β‐isopropylcinnamate could also be reduced to the corresponding dihydrocinnamate derivatives up to 98 % ee.Keywords
This publication has 72 references indexed in Scilit:
- Enantioselective Organocatalytic Indole Alkylations. Design of a New and Highly Effective Chiral Amine for Iminium CatalysisJournal of the American Chemical Society, 2002
- Enantioselective Borohydride 1,4-Reduction of α, β-Unsaturated Carboxamides Using Optically Active Cobalt(II) Complex CatalystsChemistry Letters, 1998
- Enantioselective Reduction of Electrophilic CC Bonds with sodium tetrahydroborate and ‘semicorrin’ cobalt catalystsHelvetica Chimica Acta, 1996
- From indomethacin to a selective COX-2 inhibitor: Development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitorsBioorganic & Medicinal Chemistry Letters, 1996
- Enantioselective conjugate reduction of α,β-unsaturated carboxamides with semicorrin cobalt catalystsTetrahedron: Asymmetry, 1991
- Dictionary of TerpenoidsPublished by Springer Nature ,1991
- Enantioselective Reduction of α,β‐Unsaturated Carboxylates with NaBH4 and Catalytic Amounts of Chiral Cobalt Semicorrin ComplexesAngewandte Chemie International Edition in English, 1989
- Enantioselektive Reduktion α,β‐ungesättigter Carbonsäureester mit NaBH4 und katalytischen Mengen chiraler Cobalt‐SemicorrinkomplexeAngewandte Chemie, 1989
- ABSOLUTE CONFIGURATIONS OF (+)-METHYL TODOMATUATE AND ITS NEW ANALOGUES, PSEUDOTSUGONAL AND AR-PSEUDOTSUGONAL, ISOLATED FROM DOUGLAS-FIR WOODChemistry Letters, 1973
- Terpenoids—LXTetrahedron, 1964