Asymmetric hetero-Diels-Alder reactions with heterocumulenes

Authors
Elliott, MC Monk, AE Kruiswijk, E Hibbs, DE Jenkins, RL Jones, DV
Citation
Mc. Elliott et al., Asymmetric hetero-Diels-Alder reactions with heterocumulenes, SYNLETT, (9), 1999, pp. 1379-1382
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
9
Year of publication
1999
Pages
1379 - 1382
Database
ISI
SICI code
0936-5214(199909):9<1379:AHRWH>2.0.ZU;2-6
Abstract
Chiral 2-alkenyloxazolines and 2-alkenylthiazolines react with isocyanates and ketenes to give formal hetero-Diels-Alder adducts with complete diaster eocontrol. In each case an electron-rich double bond in the adduct is prone to a second addition of the heterocumulene. In the case of the oxazoline a dducts the second addition is faster than the first, while with thiazolines the second addition is slower so that a different heterocumulene can be in corporated.