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Synthesis 1994; 1994(12): 1353-1358
DOI: 10.1055/s-1994-25693
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Carbohydrates as Chiral Auxiliaries. [2+2) Cycloadditions of Ketenes to Enol Ethers

Ingo Ganz* , Horst Kunz
  • *Institut für Organische Chemie der Universität Mainz, Becher-Weg 18-22, 55099 Mainz, Germany
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Publication Date:
25 April 2002 (online)

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Enantiomerically pure cyclobutanols containing up to four chiral centers were synthesized applying a [2+2] cycloaddition between carbohydrate enol ethers and substituted ketenes. Acid-catalysed cleavage of the anomeric acetal linkage to the carbohydrate auxiliary gave (1R,2R,3S)-3-benzyloxy-2-methylcyclobutanol in high yield and under conservation of all generated chiral centers. The absolute configuration of the synthesized cyclobutanols was determined by single-crystal X-ray analysis.