Sulfinate Allenyl Carbenoids: Synthesis of 2, 5‐Dihydrofurans by Domino Rearrangement and Cyclization. Issue 3 (18th January 2018)

• Record Type: Journal Article
• Authors: Tata, Rama Rao; Harmata, Michael
• Is Part Of: European journal of organic chemistry. Issue 3(2018)
• Page Start: 372
• Page End: 375
• Publication Date: 2018-01-18
• Subjects: Rearrangement -- Cyclization -- Dihydrofurans -- Sulfones -- Carbenoids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701743
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Propargylic sulfinates can be successfully deprotonated at the acetylenic carbon with lithium hexamethyldisilazide. The resulting anions add successfully to aldehydes and ketones. Treatment of these adducts with a silver cation results in both a 2, 3‐sigmatropic shift and a cyclization of the resulting allene to afford 2, 5‐dihydrofurans in excellent yields. Abstract : Propargylic sulfinate esters can be deprotonated at the terminal acetylenic carbon and the resulting stable organolithium species can be trapped with aldehydes and ketones. Treatment of the products with silver fluoride results in both a 2, 3‐sigmatropic shift and a heterocyclization to produce substituted 2, 5‐dihydrofurans in excellent yield.