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New Lewis acid catalysts for the Diels-Alder reaction

✍ Scribed by T. Ross Kelly; Sanat K. Maity; Premji Meghani; Nizal S. Chandrakumar

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
286 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

Catechol boron bromide (I) andferrocenium hexqpuorophosphate (2) function as Lewis acid catalysts for the Dick-Alder reaction.

The development of chiral Lewis acids as catalysts for the asymmetric induction of Diels-Alder and other reactions is a subject of current interest. Recent years have seen some progress, lV2 but no general solutions have yet emerged. In the course of studies aimed at the rational design of such catalysts it seemed useful to have new, structurally and conformationally defined sites of Lewis acidity capable of being embedded within a larger organic framework in a spatially defined manner. By appropriate manipulation of the contours of the organic scaffolding, one should then be able to design tunable, chiml environments around the Lewis acid center.

We now report that catechol boron bromide (ld and ferrocenium hexafluorophosphate (2)4 both function as Lewis acid catalysts for the Diels-Alder reaction. They also exhibit turnover. The results are summarized in

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