Chirality transfer from carbon to nitrogen to carbon via cyclic ammonium ylides

Authors
Glaeske, KW West, FG
Citation
Kw. Glaeske et Fg. West, Chirality transfer from carbon to nitrogen to carbon via cyclic ammonium ylides, ORG LETT, 1(1), 1999, pp. 31-33
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
1
Year of publication
1999
Pages
31 - 33
Database
ISI
SICI code
1523-7060(19990715)1:1<31:CTFCTN>2.0.ZU;2-0
Abstract
Cyclic ammonium salts 2 were prepared by diastereoselective quaternization of nitrogen in the corresponding proline or threonine derivatives. Upon tre atment with base, salts 2 underwent [1,2]- or [2,3]-shift to 3 with moderat e to complete stereospecificity. The overall process entails chirality tran sfer from the original alpha carbon to the neighboring nitrogen and then ba ck to the carbon.