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Synlett 1997; 1997(3): 304-306
DOI: 10.1055/s-1997-776
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Enantiopure Acetals of α-Alkynyl Carbonyl Compounds: Organoaluminum-Mediated 1,2-Shift of Cobalt-Complexed Alkynyl Group with Concomitant Capture by a Nucleophile

Kimiko Taya, Tetsuya Nagasawa, Keisuke Suzuki*
  • *Department of Chemistry, Keio University, Hiyoshi, Yokohama 223, Japan
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Publication Date:
31 December 2000 (online)

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Upon treatment with the organoaluminum-based combination of Lewis acid and nucleophile, chiral mesyloxy acetal having a Co-complexed alkynyl group undergoes stereospecific 1,2-shift of the complexed alkynyl and the concomitant attack of te ligand R of the organoaluminum reagent. Decomplexation of the products with CAN gives the chiral acetals of α-alkynyl carbonyl compounds in enantiomerically pure form in high yields.

enantiopure acetal - α-alkynyl carbonyl compounds - stereospecific 1,2-shift - Co-complexes alkynyl group