Download PDF
Synlett 1997; 1997(3): 304-306
DOI: 10.1055/s-1997-776
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

 PDF Download  Permissions and Reprints All articles of this category

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