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

Yadong Zhu; Pengfei Qian; Jiyang Yang; Shaohua Chen; Yanwei Hu; Ping Wu; Wei Wang; Wei Zhang; Shilei Zhang

doi:10.1039/c5ob00202h

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

Yadong Zhu, Pengfei Qian, Jiyang Yang, Shaohua Chen, Yanwei Hu, Ping Wu, Wei Wang, Wei Zhang, Shilei Zhang

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

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.

Original language	English (US)
Pages (from-to)	4769-4775
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	16
DOIs	https://doi.org/10.1039/c5ob00202h
State	Published - Apr 28 2015
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Organocatalytic enantioselective Michael addition of cyclic hemiacetals to nitroolefins : A facile access to chiral substituted 5- and 6-membered cyclic ethers. / Zhu, Yadong; Qian, Pengfei; Yang, Jiyang; Chen, Shaohua; Hu, Yanwei; Wu, Ping; Wang, Wei; Zhang, Wei; Zhang, Shilei.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 16, 28.04.2015, p. 4769-4775.

Research output: Contribution to journal › Article › peer-review

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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.",

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AU - Qian, Pengfei

AU - Yang, Jiyang

AU - Chen, Shaohua

AU - Hu, Yanwei

AU - Wu, Ping

AU - Wang, Wei

AU - Zhang, Wei

AU - Zhang, Shilei

PY - 2015/4/28

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AB - 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.

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

Abstract

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