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Synthesis 1996; 1996(10): 1207-1211
DOI: 10.1055/s-1996-4365
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Efficient Enantioselective Synthesis of Methyl Esters of α-Unsubstituted β-Hydroxy Acids via Asymmetric Aldol-Type Addition of Chiral Boron Enolates of (Methylthio)acetic Acid to Aldehydes

Francesco Fringuelli* , Oriana Piermatti, Ferdinando Pizzo
  • *Dipartimento di Chimica, Università di Perugia, Via Elce di Sotto 8, I-06100 Perugia, Italy
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Publication Date:
31 December 2000 (online)

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The aldol-type addition of chiral boron enolates of (methylthio)-acetic acid to various aldehydes gives α-(methylthio)-β-hydroxy acids stereoselectively and with good yields. The desulfenylation of methyl esters of the condensation adducts allows methyl esters of α-unsubstituted β-hydroxy acids to be obtained with high ee. Derivatives of (+)-2- and (+)-3-carene were used as chiral inducers. The enantioselectivity and diastereoselectivity of the aldol-type addition are efficaciously controlled by the SMe group in the α-position of the enolate and by the type of chiral ligand used.

chiral boron enolates - asymmetric aldol-type addition - chiral β-hydroxy acids - (+)-2-carene - (+)-3-carene