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A Sequential One-Pot Synthesis of Functionalized Esters and Thioesters through a Ring-Opening Acylation of Cyclic Ethers and Thioethers

Gopinath, Purushothaman and Chandrasekaran, Srinivasan (2018) A Sequential One-Pot Synthesis of Functionalized Esters and Thioesters through a Ring-Opening Acylation of Cyclic Ethers and Thioethers. In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (46). pp. 6541-6547.

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Official URL: https://doi.org/10.1002/ejoc.201801225

Abstract

A one-pot protocol for the synthesis of functionalized esters and thioesters is reported from cyclic ethers/thioethers and carboxylic acids via acyloxyphosphonium salts as key intermediates. The reaction of styrene oxide with acyloxyphosphonium salts gave complete regioselectivity and good yields of the resulting functionalized ester, whereas cyclohexene oxide gave moderate yields. Styrene episulfide, on the other hand, gave good yields with moderate regioselectivity whereas cyclohexene sulfide gave quantitative yields of the corresponding thioesters. We have also shown an alternate procedure for the ring opening of THF to form 4-bromo butyl esters. All these reactions were carried out in the absence of a catalyst, showing the synthetic versatility of our method.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to WILEY-V C H VERLAG GMBH
Keywords: Acylation; Multicomponent reactions; Synthetic methods; Functionalized esters; Thioesters
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Francis Jayakanth
Date Deposited: 10 Feb 2019 06:43
Last Modified: 10 Feb 2019 06:43
URI: http://eprints.iisc.ac.in/id/eprint/61351

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