Nonparallelism between reaction rate and dienophile-catalyst affinity in catalytic enantioselective Diels-Alder reactions.
[reaction: see text] The above reaction is much faster with Y = CF(3)CH(2)O than with Y = CH(3)O. However, the methyl ester is a strong inhibitor of the Diels-Alder reaction of the trifluoroethyl ester, since it has a higher affinity for the catalyst 1.
Ryu
Do Hyun
DH
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Zhou
Gang
G
Corey
E J
EJ