TY - JOUR
T1 - A simple route to (R)-(+)-4-t-butoxycyclopent-2-enone
AU - Eschler, Bart M.
AU - Haynes, Richard K.
AU - Kremmydas, Steve
AU - Ridley, Damon D.
PY - 1988
Y1 - 1988
N2 - (-)-10-Mercaptoisoborneol undergoes conjugate addition to racemic 4-t-butoxycyclopent-2-enone in methanol in the presence of a catalytic amount of N,N,N′,N′-tetramethylethylenediamine to give a 1:1 mixture of the sulphide adducts, which with m-chloroperbenzoic acid in ether at - 70°C is converted into a mixture of the corresponding sulphoxides; a single diastereoisomer of one of the sulphoxides is easily obtained by crystallization, and the diastereoisomer is converted by silica gel into (R)-(+)-4-t- butoxycyclopent-2-enone (1).
AB - (-)-10-Mercaptoisoborneol undergoes conjugate addition to racemic 4-t-butoxycyclopent-2-enone in methanol in the presence of a catalytic amount of N,N,N′,N′-tetramethylethylenediamine to give a 1:1 mixture of the sulphide adducts, which with m-chloroperbenzoic acid in ether at - 70°C is converted into a mixture of the corresponding sulphoxides; a single diastereoisomer of one of the sulphoxides is easily obtained by crystallization, and the diastereoisomer is converted by silica gel into (R)-(+)-4-t- butoxycyclopent-2-enone (1).
UR - https://www.webofscience.com/wos/woscc/full-record/WOS:A1988L906500038
UR - https://www.scopus.com/pages/publications/0023853885
U2 - 10.1039/C39880000137
DO - 10.1039/C39880000137
M3 - Journal Article
SN - 0022-4936
SP - 137
EP - 138
JO - Journal of the Chemical Society, Chemical Communications
JF - Journal of the Chemical Society, Chemical Communications
IS - 2
ER -