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Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans

MPS-Authors
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Xie,  Youwei
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cheng,  Gui-Juan
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Kaib,  Philip S. J.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel,  Walter
Research Department Thiel, 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

Xie, Y., Cheng, G.-J., Lee, S., Kaib, P. S. J., Thiel, W., & List, B. (2016). Catalytic Asymmetric Vinylogous Prins Cyclization: A Highly Diastereo- and Enantioselective Entry to Tetrahydrofurans. Journal of the American Chemical Society, 138(44), 14538-14541. doi:10.1021/jacs.6b09129.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002C-5A49-2
Abstract
We describe the design and development of the fi rst catalytic asymmetric vinylogous Prins cyclization. This reaction constitutes an e ffi cient approach for highly diastereo- and enantioselective synthesis of tetrahydrofur- ans (THFs) and is catalyzed by a con fi ned chiral imidodiphosphoric acid (IDP). Aromatic and heteroar- omatic aldehydes react with various 3,5-dien-1-ols to a ff ord 2,3-disubstituted THFs in excellent selectivity (d.r. > 20:1, e.r. up to 99:1). Aliphatic aldehydes react with similarly excellent results when a highly acidic imidodiphosphor- imidate (IDPi) catalyst is used. With a racemic dienyl alcohol, the reaction proceeds via a kinetic resolution. DFT calculations suggest an explanation for unusually high stereoselectivity.