Journal article
Tandem thiyl radical addition and cyclization of chiral hydrazones using a silicon-tethered alkyne
Tetrahedron: asymmetry, Vol.14(19), pp.2853-2856
2003
DOI: 10.1016/S0957-4166(03)00540-8
Abstract
A diastereoselective method for addition of a trans-2-(phenylthio)vinyl group to α-hydroxy hydrazones is presented. An ethynyl group, tethered to α-hydroxy hydrazones via a silicon tether, undergoes thiyl radical addition and cyclization under neutral tin-free conditions. In the same pot, desilylation with potassium fluoride or tetrabutylammonium fluoride affords ( E)-vinylsulfides. The one-pot process is the synthetic equivalent of an acetaldehyde Mannich reaction with acyclic stereocontrol. Graphic
Details
- Title: Subtitle
- Tandem thiyl radical addition and cyclization of chiral hydrazones using a silicon-tethered alkyne
- Creators
- Gregory K FriestadTao JiangGina M Fioroni
- Resource Type
- Journal article
- Publication Details
- Tetrahedron: asymmetry, Vol.14(19), pp.2853-2856
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/S0957-4166(03)00540-8
- ISSN
- 0957-4166
- eISSN
- 1362-511X
- Language
- English
- Date published
- 2003
- Academic Unit
- Chemistry
- Record Identifier
- 9983986088402771
Metrics
9 Record Views