Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5266422 | Tetrahedron Letters | 2013 | 4 Pages |
Abstract
The synthesis of α-methyl-β-hydroxy-δ-trichloromethyl-δ-valerolactone was achieved by an intramolecular Reformatsky reaction. The cyclisation was effected by samarium diiodide or (for the first time) ytterbium diiodide. The diastereoselectivity of the reaction corresponds to earlier investigations by Molander. Consecutive stereoselective reactions during the esterification to the Reformatsky precursor 1,1,1-trichloropent-4-en-2-yl 2-bromopropanoate and in the Reformatsky reaction itself led to (3RS,4RS,6SR)-4-hydroxy-3-methyl-6-(trichloromethyl)tetrahydro-2H-pyran-2-one (3a) as the major formed diastereomer. The influence of the orientation of the substituents in the transition state is discussed.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Thies M. Schulze, Jörg Grunenberg, Stefan Schulz,