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2. Enantioselective Cycloaddition of in SituFormed aza-Dienes and Vinyl Diazo Compounds for the Synthesis of Optically Enriched and Diazo Containing Tetrahydropyridazine

Author

Li, Song-Liang, Yang, Ting, Yin, Yi-Xiao, Karmaker, Pran Gopal, Chu, Wen-Dao, Zhou, Qing, and Liu, Quan-Zhong

Abstract

A copper catalyzed enantioselective formal aza-Diels–Alder reaction of in situformed 1,2-diaza-1,3-dienes from α-halohydrazones and vinyl diazo compounds was described. The protocol provides a variety of optically enriched diazo-containing tetrahydropyridazines in moderate yields and with up to excellent enantioselectivities. The present methodologies utilize chiral oxazolines as the chiral ligands for asymmetric catalysis and feature mild reaction conditions, readily available substrates, and broad substrate scope.

Published
2024
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6. Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans

Author

Deng, Yu-Hua, Chu, Wen-Dao, Zhang, Xiang-Zhi, Yan, Xu, Yu, Ke-Yin, Yang, Liangliang, Huang, Hanmin, Fan, Chun-An, Deng, Yu-Hua, Chu, Wen-Dao, Zhang, Xiang-Zhi, Yan, Xu, Yu, Ke-Yin, Yang, Liangliang, Huang, Hanmin, and Fan, Chun-An

Abstract

A novel enantioselective [4 + 2] annulation of the allenoates having a unique positive ortho-effect with in situ generated ortho-quinone methides has been developed under the catalysis of Cinchona alkaloid. This chiral amine-catalyzed reaction provides an alternative route to asymmetric catalytic construction of synthetically interesting, highly functionalized chiral chromans in good to excellent enantioselectivities (up to 97% ee). © 2017 American Chemical Society.

Published
2017

8. Enantioselective Formal [4+1] Cycloaddition of Diazoarylacetates and the Danishefsky's Diene: Stereoselective Synthesis of (-)-1,13-Herbertenediol.

Author

Hu F, Zhou Q, Cao F, Chu WD, He L, and Liu QZ

Abstract

Rodium chiral diene complex-catalyzed enantioselective cycloaddition of aryl α-diazoarylacetates and electron-enriched Danishefsky-type dienes afforded highly functionalized and optically enriched cyclopentenones in excellent yields (up to 97% yield) and with good to excellent enantioselectivities (60-92% ee). (-)-1,13-Herbertenediol was successfully synthesized in an overall 25% yield employing the optically enriched cyclopentenone with an all-carbon quaternary center as the key intermediate.

Published
2018
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