Challenge toward structural complexity using asymmetric catalysis: target-oriented development of catalytic enantioselective Diels-Alder reaction.
A new method for the catalytic enantioselective Diels-Alder reaction using polysubstituted silyl enol ethers as dienes is described. High enantioselectivity (up to 92% ee) was produced using a catalyst generated from FeBr(3) and AgSbF(6) in a 1:2 ratio and aryl-pybox (aryl = Ph or p-ethoxyphenyl). This reaction should facilitate the enantioselective synthesis of polycyclic acylphloroglucinols such as hyperforin or garsubellin A, which are currently of interest from synthetic and medicinal points of view.
Usuda
Hiroyuki
H
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
Kuramochi
Akiyoshi
A
Kanai
Motomu
M
Shibasaki
Masakatsu
M