화학공학소재연구정보센터
Journal of the American Chemical Society, Vol.139, No.39, 13656-13659, 2017
Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes
Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Bronsted acid catalysts of the hetero-Diels-Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereo selectivity is generally observed and a variety of scents and natural products can be easily accessed.