With solid phase organic synthesis method(SPOS), polymer-bound N-enoylprolinol(4) was prepared by the attachment of N-enoylprolinol(3) to Merrifield resin and was used for asymmetric Michael additions for the first time. The enantiomeric excess obtained by this method is increased as compared with that obtained by the corresponding solution phase reactions.
R ) and ( S ) 4 Methyl 1 nonanol, the sex attractant of the yellow mealworn( Tenebrio molitor L. ), were synthesized from bornane 10,2 sultam via asymmetric alkylation of N acylbornane 10,2 sultam with alkyl iodide, reductive cleavage with LiAlH 4, bromination with HBr and reaction of organocuprate reagent with ethylene oxide in the presence of BF 3·Et 2O. The enantiomeric excess of the total syntheses was over 97%e.e..
Started from 5-hydroxy-2-pentanone, (R)(E)-3,7-dimethyl-2-octene-1,8-dioic acid, callosobruchusic acid, was synthesized via five steps with D-(-)-camphor sultam as the chiral auxiliary. It was of good optical purity and yield.
YU Guang-ao, HUANG Jin-xia **, HOU Jun-li, Li Yan and XU Zhang-huangDepartment of Chemistry, Hubei University, Wuhan 430062, P. R. China
