Angewandte Chemie - International Edition p. 7703 - 7706 (2015)
Update date:2022-08-03
Topics:
Tsui, Gavin Chit
Liu, Luping
List, Benjamin
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. A bulky cat.: In an organocatalytic asymmetric Prins cyclization, salicylaldehydes react with 3-methyl-3-buten-1-ol in the presence of a chiral imidodiphosphoric acid catalyst to afford highly functionalized 4-methylenetetrahydropyrans in excellent regio- and enantioselectivities (see scheme).
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