Issue 51, 2017

Highly enantioselective synthesis of fused bicyclic dihydropyranones via low-loading N-heterocyclic carbene organocatalysis

Abstract

Highly diastereo and enantioselective [4+2] cycloadditions have been achieved between pyrrolidone-derived cyclic enones and α-haloaldehydes under mild conditions. Relying on extremely reactive in-situ generated chiral N-heterocyclic carbenes, this stereoselective annulation proceeds efficiently even on the gram scale with the catalyst loading as low as 0.025 mol% (250 ppm). A variety of cis-substituted bicyclic dihydropyranones can be produced in up to 96% yield with up to >99% ee. In addition, simple, inexpensive linear aldehydes such as n-propanal can be used directly in asymmetric cycloadditions via oxidative N-heterocyclic carbene organocatalysis with low catalyst loading. This method may provide an economical and practical approach for the asymmetric synthesis of medicinally relevant molecules.

Graphical abstract: Highly enantioselective synthesis of fused bicyclic dihydropyranones via low-loading N-heterocyclic carbene organocatalysis

Supplementary files

Article information

Article type
Communication
Submitted
16 Apr 2017
Accepted
05 Jun 2017
First published
05 Jun 2017

Chem. Commun., 2017,53, 6875-6878

Highly enantioselective synthesis of fused bicyclic dihydropyranones via low-loading N-heterocyclic carbene organocatalysis

J. Li, L. Fu, J. Wu, K. Yang, Q. Li, X. Gou, C. Peng, B. Han and X. Shen, Chem. Commun., 2017, 53, 6875 DOI: 10.1039/C7CC02921G

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