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Synlett 1990; 1990(7): 397-398
DOI: 10.1055/s-1990-21104
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Formation of Cyclopentane Derivatives by Mukaiyama's Reaction of Bisketene Silyl Acetals

Syed Masarrat Ali* , Gérard Rousseau
  • *Laboratoire des Carbocycles, U.A. CNRS 478, Université de Paris-Sud, Bât.420, F-91405 Orsay, France
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Publication Date:
08 March 2002 (online)

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The aldol-type reaction of bisketene silyl acetals derived from glutarates with 1,2-diketones in presence of titanium(IV) chloride in dichloromethane at -80 °C leads to the formation of various 4,5-dihydroxy-1,3-cyclopentanedicarboxylates. The reaction appears to be stereoselective. Under these conditions, formation of higher membered rings is not observed.