High diastereoselective synthesis of spiro-barbituratechromans via domino oxa-Michael/1,6-addition reactions of ortho-hydroxyphenylsubstituted para-quinone methides with barbiturate-based olefins

A novel Et3N-catalyzed domino oxa-Michael/1,6-addition reaction of ortho-hydroxyphenylsubstituted p-QMs with barbiturate-based olefins is achieved under mild conditions. Various new spiro-barbituratechromans were obtained in excellent yields and diastereoselectivities (90–99% yield, >99:1 dr). Th...

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Published in:Tetrahedron 2019-12, Vol.75 (51), p.130752, Article 130752
Main Authors: Huo, Mingming, Zhou, Jing, Bai, Lijuan, Xu, Qigui, Zhou, Zhihong, Zhou, Hui, Liang, Guojuan
Format: Article
Language:English
Subjects:
Barbiturate-based olefins
Domino reaction
ortho-Hydroxyphenylsubstituted p-QMs
Oxa-Michael/1,6-addition
Spiro-barbituratechromans
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cited_by cdi_FETCH-LOGICAL-c297t-2aeb296beadf461f05d358d02e091eeb363c2b2fe679709ce464a1224d3804d33
cites cdi_FETCH-LOGICAL-c297t-2aeb296beadf461f05d358d02e091eeb363c2b2fe679709ce464a1224d3804d33
container_end_page
container_issue 51
container_start_page 130752
container_title Tetrahedron
container_volume 75
creator Huo, Mingming
Zhou, Jing
Bai, Lijuan
Xu, Qigui
Zhou, Zhihong
Zhou, Hui
Liang, Guojuan
description A novel Et3N-catalyzed domino oxa-Michael/1,6-addition reaction of ortho-hydroxyphenylsubstituted p-QMs with barbiturate-based olefins is achieved under mild conditions. Various new spiro-barbituratechromans were obtained in excellent yields and diastereoselectivities (90–99% yield, >99:1 dr). The structure of the new compound 3a was determined by single crystal X-ray analysis. [Display omitted] •Et3N catalyzed oxa-Michael/1,6-addition reactions of ortho-hydroxyphenylsubstituted p-QMs with barbiturate-derived alkenes.•A wide range of new spiro-barbituratechromans were constructed in excellent yields and diastereoselectivities.•The structure of the new compound 3a was determined by single crystal X-ray analysis.
doi_str_mv 10.1016/j.tet.2019.130752
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subjects Barbiturate-based olefins
Domino reaction
ortho-Hydroxyphenylsubstituted p-QMs
Oxa-Michael/1,6-addition
Spiro-barbituratechromans
title High diastereoselective synthesis of spiro-barbituratechromans via domino oxa-Michael/1,6-addition reactions of ortho-hydroxyphenylsubstituted para-quinone methides with barbiturate-based olefins
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