Complete pi-facial diastereoselectivity in Diels-Alder reactions of dissymmetric 2,4-cyclohexadienones.
[reaction: see text] The studies in the Diels-Alder reactions of 5-methoxy-masked o-benzoquinone (1a, R = OMe) and simple dissymmetric 2,4-cyclohexadienones 1b-e with methyl vinyl ketone, styrene, and benzyl vinyl ether are described. The dienones 1b-e reacted with dienophiles to form syn adducts (dienophile approach is syn to allylic methoxy group) exclusively.
Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan, Republic of China.
Hui-Fang
HF
Hou
Rama Krishna
RK
Peddinti
Chun-Chen
CC
Liao