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Synlett 1999; 1999(12): 1999-2003
DOI: 10.1055/s-1999-2972
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Facile Preparation of (Phosphorylalkyl)-Functionalized Cyclopropanols and Cyclopropylamines

Harald Winsel* , Vesta Gazizova, Oleg Kulinkovich, Valeriy Pavlov, Armin de Meijere
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany; E-mail: ameijer1@uni-goettingen.de
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Publication Date:
31 December 1999 (online)

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The reactions of esters 1 and dialkylamides 8 of 3-phosphorylpropionic acids with Grignard reagents 6 in the presence of titanium tetraisopropoxide 5 or methyltitanium triisopropoxide 11 give 1-substituted and 1,2-disubstituted phosphorylated cyclopropanols 7 and cyclopropylamines 12 in moderate to very good yields (37-71 and 39-86%, respectively). These useful transformations convincingly demonstrate the wide functional group compatibility and versatility of this new carbonyl group cyclopropanation.

cyclopropanations - titanium-mediated - ligand exchange - phosphonates - phosphine oxides - aminophosphonic acids