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The Organocatalytic Asymmetric Prins Cyclization.

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Tsui,  Garvin Chit
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Liu,  Luping
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Tsui, G. C., Liu, L., & List, B. (2015). The Organocatalytic Asymmetric Prins Cyclization. Angewandte Chemie International Edition, 54(26), 7703-7706. doi:10.1002/anie.201500219.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0028-30E4-9
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.