Enantioselective and structure-selective Diels-Alder reactions of unsymmetrical quinones catalyzed by a chiral oxazaborolidinium cation. Predictive selection rules.
The chiral oxazaborolidinium cation 1 promotes Diels-Alder reactions between 2-triisopropylsilyloxy-1,3-butadiene and a number of unsymmetrical 1,4-benzoquinones in a highly enantioselective and structurally selective manner. The basis for the enantioselectivity is explained rationally in terms of a preferred type of transition-state assembly. Selection rules have been developed that allow the prediction of the principal reaction product of Diels-Alder reaction between unsymmetrical diene and quinone components.
Ryu
Do Hyun
DH
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Zhou
Gang
G
Corey
E J
EJ