Issue 16, 2015

Organocatalytic enantioselective Michael addition of cyclic hemiacetals to nitroolefins: a facile access to chiral substituted 5- and 6-membered cyclic ethers

Abstract

An efficient aminocatalytic enantioselective Michael addition of readily available cyclic hemiacetals to nitroolefins has been developed. The strategy serves as a powerful approach to synthetically valuable chiral 3-substituted tetrahydrofurans (THFs) and tetrahydropyrans (THPs). The synthetic utilities of the versatile Michael adducts also have been demonstrated in the synthesis of 2,3-disubstituted cyclic ethers, α-substituted lactones and venlafaxine analogues.

Graphical abstract: Organocatalytic enantioselective Michael addition of cyclic hemiacetals to nitroolefins: a facile access to chiral substituted 5- and 6-membered cyclic ethers

Supplementary files

Article information

Article type
Paper
Submitted
01 Feb 2015
Accepted
06 Mar 2015
First published
06 Mar 2015

Org. Biomol. Chem., 2015,13, 4769-4775

Author version available

Organocatalytic enantioselective Michael addition of cyclic hemiacetals to nitroolefins: a facile access to chiral substituted 5- and 6-membered cyclic ethers

Y. Zhu, P. Qian, J. Yang, S. Chen, Y. Hu, P. Wu, W. Wang, W. Zhang and S. Zhang, Org. Biomol. Chem., 2015, 13, 4769 DOI: 10.1039/C5OB00202H

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