Enantioselective and Structure-Selective Diels−Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules
Journal of the American Chemical SocietyPublished 25 March 2004
Do Hyun Ryu, Gang Zhou, E. J. Corey
Citations131
SJR quartileQ1
SJR score5.55
SNIP2.61
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Abstract
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.
Keywords
Chemistry
Journal of the American Chemical SocietyAsymmetric Diels−Alder Reactions Catalyzed by a Triflic Acid Activated Chiral Oxazaborolidine
280 Citations2002E. J. Corey, Takanori Shibata +1 more
The absolute stereochemical course of the Diels-Alder reactions catalyzed by 6A and 6B was successfully predicted on the basis of the mechanistic principles which have recently been formulated for this type of catalytic enantioselective reaction involving re-face attack by the diene on complex 7.