1231934-42-1Relevant articles and documents
Insights into the stereoselective BF3-catalyzed hetero Diels-Alder reaction of Garner's aldehyde with Danishefsky's diene
Fontana, Carolina,Incerti, Marcelo,Moyna, Guillermo,Manta, Eduardo
, p. 398 - 404 (2010)
A trans-2,6-disubstituted tetrahydropyranone was prepared in high yield via a BF3-mediated hetero Diels-Alder reaction between Danishefsky's diene and Garner's aldehyde. Only two of the four possible reaction products were obtained, and excellent diastereoselectivity toward the exo-syn adduct was observed (de = 80%). The origin of this somewhat unusual selectivity can be attributed to the steric interactions between the bulky protecting groups present in the diene and dienophile.