One-Pot Synthesis of Cyclopentenols from Vinylethylene Carbonates via Palladium-Catalyzed Decarboxylative Allylation and Cascade Oxidation-Cyclization

An efficient, one-pot protocol for the synthesis of highly functionalized cyclopentenols has been accomplished starting from vinylethylene carbonates and bissulfonylmethanes. This protocol proceeds via sequential palladium-catalyzed decarboxylative allylation and oxidative cyclization in an operatio...

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Veröffentlicht in:	Bulletin of the Chemical Society of Japan 2022-04, Vol.95 (4), p.634-638
Hauptverfasser:	Zhang, Ke, Ke, Miaolin, Liu, Zhigang, Zuo, Sheng, Chen, Fen-er
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols Allyl compounds Carbonates Chemical reactions Oxidation Palladium Selectivity Substrates
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creator	Zhang, Ke Ke, Miaolin Liu, Zhigang Zuo, Sheng Chen, Fen-er
description	An efficient, one-pot protocol for the synthesis of highly functionalized cyclopentenols has been accomplished starting from vinylethylene carbonates and bissulfonylmethanes. This protocol proceeds via sequential palladium-catalyzed decarboxylative allylation and oxidative cyclization in an operationally simple manner. A wide range of substrates is well-accommodated to afford diverse cyclopentenols in moderate to good yields with excellent selectivity. Further control experiments demonstrated that the selective formation of the isolatable (Z)-allyl alcohols (up to Z/E = >19:1) underlies the success of the subsequent cascade oxidation-cyclization.
doi_str_mv	10.1246/bcsj.20210451
format	Article
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source	Oxford University Press Journals All Titles (1996-Current)
subjects	Alcohols Allyl compounds Carbonates Chemical reactions Oxidation Palladium Selectivity Substrates
title	One-Pot Synthesis of Cyclopentenols from Vinylethylene Carbonates via Palladium-Catalyzed Decarboxylative Allylation and Cascade Oxidation-Cyclization
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