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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Veröffentlicht in:	Tetrahedron letters 2011-10, Vol.52 (41), p.5359-5362
Hauptverfasser:	Veeraraghavan Ramachandran, P., Parthasarathy, Gowrisankar, Gagare, Pravin D.
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Zusammenfassung:	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