(Alkylthio)alkynes as addends in the Co(0) catalyzed intramolecular Pauson-Khand reaction. Substituent driven enhancements of annulation efficiency and stereoselectivity

Authors
Pagenkopf, BL Belanger, DB O'Mahony, DJR Livinghouse, T
Citation
Bl. Pagenkopf et al., (Alkylthio)alkynes as addends in the Co(0) catalyzed intramolecular Pauson-Khand reaction. Substituent driven enhancements of annulation efficiency and stereoselectivity, SYNTHESIS-S, (7), 2000, pp. 1009-1019
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
7
Year of publication
2000
Pages
1009 - 1019
Database
ISI
SICI code
0039-7881(2000):7<1009:(AAITC>2.0.ZU;2-S
Abstract
Compared to terminal alkynes, (methylthio)alkynes are generally superior su bstrates for the thermally promoted, Co-2(CO)(8) catalyzed Pauson-Khand rea ction of enynes and allenynes, providing enones in higher yields and with e nhanced diastereoselectivity. Improvements in yield dependent upon the use of 2,2,2-trifluoroethanol as co-solvent and an apparent preference for endo selectivity with (ethoxy)alkynes are also disclosed.