Construction of Enantioenriched γ,γ-Disubstituted Butenolides Enabled by Chiral Amine and Lewis Acid Cascade Cocatalysis

Chenguang Yu; Peng Ji; Yueteng Zhang; Xiang Meng; Wei Wang

doi:10.1021/acs.orglett.1c02916

Construction of Enantioenriched γ,γ-Disubstituted Butenolides Enabled by Chiral Amine and Lewis Acid Cascade Cocatalysis

Chenguang Yu, Peng Ji, Yueteng Zhang, Xiang Meng, Wei Wang

Pharmacology and Toxicology

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

7 Scopus citations

Abstract

Herein we report a cascade cocatalysis strategy for the facile construction of chiral γ,γ-disubstituted butenolides. The synthetic manifold employs simple alkynoic acids instead of the preformed silyloxy furans or 5-substituted furan-2(3H)-ones. In situ formed 5-substituted furan-2(3H)-ones by AgNO3 or Ph3PAuCl/AgOTf catalyzed cyclization of alkynoic acids can smoothly engage in the subsequent chiral diphenylprolinol TMS-ether catalyzed Michael and Michael-aldol reactions. The cascade process serves as a general approach to chiral quaternary γ,γ-disubstituted butenolides.

Original language	English (US)
Pages (from-to)	7656-7660
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.1c02916
State	Published - Oct 1 2021

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Construction of Enantioenriched γ,γ-Disubstituted Butenolides Enabled by Chiral Amine and Lewis Acid Cascade Cocatalysis",

abstract = "Herein we report a cascade cocatalysis strategy for the facile construction of chiral γ,γ-disubstituted butenolides. The synthetic manifold employs simple alkynoic acids instead of the preformed silyloxy furans or 5-substituted furan-2(3H)-ones. In situ formed 5-substituted furan-2(3H)-ones by AgNO3 or Ph3PAuCl/AgOTf catalyzed cyclization of alkynoic acids can smoothly engage in the subsequent chiral diphenylprolinol TMS-ether catalyzed Michael and Michael-aldol reactions. The cascade process serves as a general approach to chiral quaternary γ,γ-disubstituted butenolides.",

author = "Chenguang Yu and Peng Ji and Yueteng Zhang and Xiang Meng and Wei Wang",

note = "Funding Information: Financial support was provided by the NIH (5R01GM125920-04) and the NSF MRI for acquisition of a 500 MHz NMR spectrometer (1920234). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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T1 - Construction of Enantioenriched γ,γ-Disubstituted Butenolides Enabled by Chiral Amine and Lewis Acid Cascade Cocatalysis

AU - Yu, Chenguang

AU - Ji, Peng

AU - Zhang, Yueteng

AU - Meng, Xiang

AU - Wang, Wei

N1 - Funding Information: Financial support was provided by the NIH (5R01GM125920-04) and the NSF MRI for acquisition of a 500 MHz NMR spectrometer (1920234). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/10/1

Y1 - 2021/10/1

N2 - Herein we report a cascade cocatalysis strategy for the facile construction of chiral γ,γ-disubstituted butenolides. The synthetic manifold employs simple alkynoic acids instead of the preformed silyloxy furans or 5-substituted furan-2(3H)-ones. In situ formed 5-substituted furan-2(3H)-ones by AgNO3 or Ph3PAuCl/AgOTf catalyzed cyclization of alkynoic acids can smoothly engage in the subsequent chiral diphenylprolinol TMS-ether catalyzed Michael and Michael-aldol reactions. The cascade process serves as a general approach to chiral quaternary γ,γ-disubstituted butenolides.

AB - Herein we report a cascade cocatalysis strategy for the facile construction of chiral γ,γ-disubstituted butenolides. The synthetic manifold employs simple alkynoic acids instead of the preformed silyloxy furans or 5-substituted furan-2(3H)-ones. In situ formed 5-substituted furan-2(3H)-ones by AgNO3 or Ph3PAuCl/AgOTf catalyzed cyclization of alkynoic acids can smoothly engage in the subsequent chiral diphenylprolinol TMS-ether catalyzed Michael and Michael-aldol reactions. The cascade process serves as a general approach to chiral quaternary γ,γ-disubstituted butenolides.

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Construction of Enantioenriched γ,γ-Disubstituted Butenolides Enabled by Chiral Amine and Lewis Acid Cascade Cocatalysis

Abstract

ASJC Scopus subject areas

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