Abstract
Diastereoselective Diels-Alder reactions. The role of the catalyst
Highlights
The importance of the asymmetric Lewis acid-catalyzed Diels-Alder and hetero-Diels Alder reactions in organic synthesis has been emphasized in a number of recent reviews.[2]
Catalysis of the same reaction by EtAlCl2 resulted in the product of α−si-face addition preferentially leading to 4 (98:2)
The decrease in diastereoselection that is observed when excess EtAlCl2 is used is consistent with the intermediacy of a chelate in which the aluminum is pentacoordinate and the excess Lewis acid complexes to produce a species with essentially the same facial selectivity as that formed from Et2AlCl
Summary
The importance of the asymmetric Lewis acid-catalyzed Diels-Alder and hetero-Diels Alder reactions in organic synthesis has been emphasized in a number of recent reviews.[2]. We report a more comprehensive evaluation of this reaction with a number of common Lewis acids and computations which allow us to suggest that the diastereoselectivity may be predicted.
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