Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes

Ding Zhou; Xueting Yu; Jian Zhang; Wei Wang; Hexin Xie

doi:10.1021/acs.orglett.7b03539

Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes

Ding Zhou, Xueting Yu, Jian Zhang, Wei Wang, Hexin Xie

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

23 Scopus citations

Abstract

An unprecedented chiral secondary amine-catalyzed formal [4 + 2] annulation of aldehydes and oxidation-generated β-unsubstituted o-QMs is reported. This asymmetric protocol allows direct functionalization of the benzylic C-H bonds and furnishes [4 + 2] cycloadducts, chromanols, with excellent enantioselectivity and in up to 92% yield. The usability of this approach was further demonstrated by the enantioselective synthesis of anticancer Rhinacanthins derivative NKPLS8.

Original language	English (US)
Pages (from-to)	174-177
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.7b03539
State	Published - Jan 5 2018
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes",

abstract = "An unprecedented chiral secondary amine-catalyzed formal [4 + 2] annulation of aldehydes and oxidation-generated β-unsubstituted o-QMs is reported. This asymmetric protocol allows direct functionalization of the benzylic C-H bonds and furnishes [4 + 2] cycloadducts, chromanols, with excellent enantioselectivity and in up to 92% yield. The usability of this approach was further demonstrated by the enantioselective synthesis of anticancer Rhinacanthins derivative NKPLS8.",

author = "Ding Zhou and Xueting Yu and Jian Zhang and Wei Wang and Hexin Xie",

note = "Funding Information: We are thankful to the “Thousand Plan” Youth Program, the Fundamental Research Funds for the Central Universities, and the East China University of Science and Technology for financial support. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b03539",

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T1 - Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes

AU - Zhou, Ding

AU - Yu, Xueting

AU - Zhang, Jian

AU - Wang, Wei

AU - Xie, Hexin

N1 - Funding Information: We are thankful to the “Thousand Plan” Youth Program, the Fundamental Research Funds for the Central Universities, and the East China University of Science and Technology for financial support. Publisher Copyright: © 2017 American Chemical Society.

PY - 2018/1/5

Y1 - 2018/1/5

N2 - An unprecedented chiral secondary amine-catalyzed formal [4 + 2] annulation of aldehydes and oxidation-generated β-unsubstituted o-QMs is reported. This asymmetric protocol allows direct functionalization of the benzylic C-H bonds and furnishes [4 + 2] cycloadducts, chromanols, with excellent enantioselectivity and in up to 92% yield. The usability of this approach was further demonstrated by the enantioselective synthesis of anticancer Rhinacanthins derivative NKPLS8.

AB - An unprecedented chiral secondary amine-catalyzed formal [4 + 2] annulation of aldehydes and oxidation-generated β-unsubstituted o-QMs is reported. This asymmetric protocol allows direct functionalization of the benzylic C-H bonds and furnishes [4 + 2] cycloadducts, chromanols, with excellent enantioselectivity and in up to 92% yield. The usability of this approach was further demonstrated by the enantioselective synthesis of anticancer Rhinacanthins derivative NKPLS8.

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Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes

Abstract

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