A Sequential One‐Pot Synthesis of Functionalized Esters and Thioesters through a Ring‐Opening Acylation of Cyclic Ethers and Thioethers. Issue 46 (30th November 2018)

• Record Type: Journal Article
• Authors: Gopinath, Purushothaman; Chandrasekaran, Srinivasan
• Is Part Of: European journal of organic chemistry. Issue 46(2018)
• Page Start: 6541
• Page End: 6547
• Publication Date: 2018-11-30
• Subjects: Acylation -- Multicomponent reactions -- Synthetic methods -- Functionalized esters -- Thioesters; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801225
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : Functionalized esters and thioesters were synthesized from carboxylic acids and cyclic ethers/thioethers via acyloxyphosphonium salts as key intermediates. The resulting esters were obtained in high yields and with complete regioselectivity (for styrene oxide). Thioesters were obtained in good yields but with moderate regioselectivity (for styrene episulfide).