This work was supported by the Fonds der Chemischen Industrie and the Universität Göttingen. H. G. thanks the Fonds der Chemischen Industrie for a doctoral fellowship. We thank Professor Tietze for his generous support and continuous interest.
Article first published online: 22 DEC 2003
Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 34, Issue 6, pages 647–649, March 31, 1995
How to Cite
Beifuss, U., Gehm, H., Noltemeyer, M. and Schmidt, H.-G. (1995), Sequential Transformation of Benzothiopyrylium Salts to Diastereoselectively Annulated Benzothiopyranones. Angew. Chem. Int. Ed. Engl., 34: 647–649. doi: 10.1002/anie.199506471
Dedicated to Professor Wolfgang Lüttke on the occasion of his 75th birthday
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 22 JUL 1995
- cascade reactions;
- sulfur compounds;
As many as three stereogenic centers were introduced in one step in the preparatively simple cascade reaction of 1-benzothiopyrylium salts with 2-siloxy-1,3-butadienes. The cascade comprises 1,2-additions and subsequent intramolecular 1,4-additions and gives the all-cis-thioxanthon rac-3 in 91% yield from the starting compounds 1 and 2, formed in situ. A diastereoselective synthesis of such compounds was not previously known.