DIASTEREOSELECTIVE SYNTHESIS OF 3,6-DIHYDRO-2H-1,3,4-THIADIAZINES

Authors
CHARRIER JD RELIQUET A MESLIN JC
Citation
Jd. Charrier et al., DIASTEREOSELECTIVE SYNTHESIS OF 3,6-DIHYDRO-2H-1,3,4-THIADIAZINES, Tetrahedron : asymmetry, 9(9), 1998, pp. 1531-1537
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
9
Year of publication
1998
Pages
1531 - 1537
Database
ISI
SICI code
0957-4166(1998)9:9<1531:DSO3>2.0.ZU;2-4
Abstract
Thionation of the benzil hydrazones 3 with Lawesson's reagent afforded the 3,6-dihydro-2H-1,3,4-thiadiazines 4 by an intramolecular cyclisat ion. This reaction was shown to be diastereospecific and allowed the f ormation of the exo compounds 4b-e. When the homochiral SAMP-hydrazone 3f was used, the reaction afforded enantiomerically pure (4R,6R,9S)-4 f. (C) 1998 Elsevier Science Ltd. All rights reserved.