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Synlett 1997; 1997(8): 977-979
DOI: 10.1055/s-1997-5790
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Diastereoselective Synthesis of Cyclopropyl Boronic Esters

Jörg Pietruszka* , Markus Widenmeyer
  • *Institut für Organische Chemie und Isotopenforschung, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax: +711 685 4321; E-mail: joerg.pietruszka@po.uni-stuttgart.de
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Publication Date:
31 December 2000 (online)

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The conversion of simple 1-alkynes to optically active 2-alkyl-cyclopropan-1-ols is conveniently achieved by a simple protocol. The key step is the cyclopropanation of alkenyl boronic esters derived from (+)-diisopropyl L-tartrate and alkenyl boronic acids. It has been found that best yields could be obtained using diazomethane and palladium(II) acetate as catalyst. The systematic investigation of parameters influencing this reaction led to an improvement of the diastereoselectivity of the transformation.

cyclopropanation - cyclopropyl boronic ester - diazomethane - cyclopropanol - diisopropyl tartrate