Diastereoselective vinyl addition to chiral hydrazones via tandem thiyl radical addition and silicon-tethered cyclization

Authors
Friestad, GK Massari, SE
Citation
Gk. Friestad et Se. Massari, Diastereoselective vinyl addition to chiral hydrazones via tandem thiyl radical addition and silicon-tethered cyclization, ORG LETT, 2(26), 2000, pp. 4237-4240
Citations number
84
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
26
Year of publication
2000
Pages
4237 - 4240
Database
ISI
SICI code
1523-7060(200012)2:26<4237:DVATCH>2.0.ZU;2-2
Abstract
[GRAPHICS] A diastereoselective method for addition of a vinyl group to cc-hydroxy hyd razones under neutral tin-free radical cyclization conditions, leading to s ubstituted vinylglycinols, is presented. Tandem thiyl radical addition/cycl ization upon a silicon-tethered vinyl group followed by treatment with pota ssium fluoride accomplishes a one pot neutral vinyl addition process to aff ord acyclic allylic anti-hydrazino alcohols in good yield.