Organic letters

Distant functionalization via incorporation of thiophene moieties in electrophilic reactions promoted by samarium diiodide

SM Yang, SK Nandy, AR Selvakumar, JM Fang

Index: Yang, Shyh-Ming; Nandy, Sandip Kumar; Selvakumar, Anandakathir Robinson; Fang, Jim-Min Organic Letters, 2000 , vol. 2, # 23 p. 3719 - 3721

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Citation Number: 10

Abstract

Methyl thiophene-2-carboxylate, methyl 3-(thien-2-yl) acrylate, and methyl 5, 2'-bithiophene- 2-carboxylate were utilized as the synthetic equivalents of pentanoate 5-anion, pentanoate 4, 5-dianion, heptanoate 7-anion, and nonanoate-8, 9-dianion. By the promotion of samarium diiodide, these thiophene-incorporating compounds reacted with aldehydes, ketones, and conjugated esters regioselectively at the thienyl rings. Long-chain esters ...