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Free keywords:
asymmetric catalysis; Brønsted acids; organocatalysis; Prins cyclization; tetrahydropyrans
Abstract:
We describe here the design and development of an organocatalytic Prins cyclization. In the presence of a confined chiral imidodiphosphoric acid catalyst, salicylaldehydes react with 3-methyl-3-buten-1-ol to afford highly functionalized 4-methylenetetrahydropyrans in excellent regio- and enantioselectivity. The extreme steric demand of the acid catalyst is key for the success of this transformation.