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Issue 34, 2020
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Highly diastereoselective synthesis of 3-methylenetetrahydropyrans by palladium-catalyzed oxa-[4 + 2] cycloaddition of 2-alkenylbenzothiazoles

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Abstract

A highly diastereoselective synthesis of 3-methylenetetrahydropyrans via palladium-catalyzed oxa-[4 + 2] cycloaddition of 2-alkenylbenzothiazoles with allyl carbonates bearing a nucleophilic alcohol side chain is presented. This synthetic methodology tolerates a wide variety of 2-alkenylbenzothiazoles and afforded the desired 3-methylenetetrahydropyrans in good yields and excellent dr. In addition, further derivatizations resulted in new scaffolds, making them useful synthetic precursors.

Graphical abstract: Highly diastereoselective synthesis of 3-methylenetetrahydropyrans by palladium-catalyzed oxa-[4 + 2] cycloaddition of 2-alkenylbenzothiazoles

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Article information


Submitted
11 Jul 2020
Accepted
17 Aug 2020
First published
18 Aug 2020

Org. Biomol. Chem., 2020,18, 6617-6621
Article type
Communication

Highly diastereoselective synthesis of 3-methylenetetrahydropyrans by palladium-catalyzed oxa-[4 + 2] cycloaddition of 2-alkenylbenzothiazoles

X. Song, L. Xu and Q. Ni, Org. Biomol. Chem., 2020, 18, 6617
DOI: 10.1039/D0OB01434F

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