1,2-ASYMMETRIC INDUCTION IN A NEW TANDEM OF (3,3)-SIGMATROPIC REARRANGEMENT OF ALLYLIC THIOCYANATES AND INTRAMOLECULAR AMINE ADDITION TO N=C=S GROUP

Authors
MARTINKOVA M GONDA J
Citation
M. Martinkova et J. Gonda, 1,2-ASYMMETRIC INDUCTION IN A NEW TANDEM OF (3,3)-SIGMATROPIC REARRANGEMENT OF ALLYLIC THIOCYANATES AND INTRAMOLECULAR AMINE ADDITION TO N=C=S GROUP, Tetrahedron letters, 38(5), 1997, pp. 875-878
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
5
Year of publication
1997
Pages
875 - 878
Database
ISI
SICI code
0040-4039(1997)38:5<875:1IIANT>2.0.ZU;2-0
Abstract
A new synthetic route to diastetereomerically pure 1,3-imidazolidin-2- thiones via a tandem of (3,3)-sigmatropic rearrangement of chiral thio cyanates followed by stereoselective intramolecular amine addition to arising isothiocyanates is reported The semiempirical AM1 calculations demonstrate that the observed diastereoselectivity is entirely consis tent with the energy difference between diastereomeric transition stat es of heterocyclisation step. (C) 1997, Published by Elsevier Science Ltd.