SYNTHESIS OF ENANTIOMERICALLY PURE 2,3-DISUBSTITUTED OXIRANE-2-CARBOXAMIDES

Authors
RUANO JLG CASTRO AMM RAMOS JHR FLAMARIQUE ACR
Citation
Jlg. Ruano et al., SYNTHESIS OF ENANTIOMERICALLY PURE 2,3-DISUBSTITUTED OXIRANE-2-CARBOXAMIDES, Tetrahedron : asymmetry, 8(20), 1997, pp. 3503-3511
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
20
Year of publication
1997
Pages
3503 - 3511
Database
ISI
SICI code
0957-4166(1997)8:20<3503:SOEP2O>2.0.ZU;2-0
Abstract
The title compounds were efficiently prepared from 1-alkyl(or phenyl)- 2-methyl-2-(tolylsulfinyl)ethanone through a simple four-step sequence : highly stereoselective hydrocyanation with Et2AlCN (key step to cont rol the stereochemistry); hydrolysis to sulfinylamides and separation of epimers; reduction of the sulfur functionality; and final cyclizati on to enantiopure oxirane derivatives. (C) 1997 Elsevier Science Ltd.