Practical synthesis and highly diastereoselective Diels-Alder reactions of 1-alkylthio-3-silyloxybutadienes.
An efficient acid-catalyzed method for the synthesis of vinylogous thioesters was developed. 1-Alkylthio-3-silyloxybutadienes were then produced in high yields from the corresponding vinylogous thioesters. These dienes were highly reactive in Diels-Alder reactions, affording the cycloadducts in high endo selectivity under mild conditions.
Holmes
Janice M
JM
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, S7N 5C9, Canada.
Albert
Andrea L
AL
Gravel
Michel
M