Preparation and application of 2-(arylmethoxy)isopinocampheols for the asymmetric aldol reaction of 3,3,3-trifluoropropionates

The preparation of 2-(arylmethoxy)isopinocampheols from pinanediol via the DIABL-H reduction of the corresponding aryl aldehyde acetals has been described. A systematic examination of the asymmetric aldol reaction of 3,3,3-trifluoropropionates led to the double diastereoselective aldol reaction of 2...

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Bibliographic Details
Published in:Tetrahedron letters 2011-10, Vol.52 (41), p.5359-5362
Main Authors: Veeraraghavan Ramachandran, P., Parthasarathy, Gowrisankar, Gagare, Pravin D.
Format: Article
Language:English
Subjects:
Acetals
Aldehydes
Aldol
Alicyclic compounds, terpenoids, prostaglandins, steroids
Aromatic compounds
Asymmetry
Boron enolates
Chemistry
Diisopinocampheylboron triflate
Esters
Exact sciences and technology
Isopinocampheols
Organic chemistry
Preparations and properties
Reduction
Terpenoids
Tetrahedrons
Trifluoropropionates
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Summary:The preparation of 2-(arylmethoxy)isopinocampheols from pinanediol via the DIABL-H reduction of the corresponding aryl aldehyde acetals has been described. A systematic examination of the asymmetric aldol reaction of 3,3,3-trifluoropropionates led to the double diastereoselective aldol reaction of 2-(arylmethoxy)isopinocampheyl 3,3,3-trifluoropropionates providing anti-α-trifluoromethyl-β-hydroxy esters in 63–85% yields, ⩾99% anti-selectivity and 80–96% de for the anti-isomer.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.08.034