Stereoselective Reductive Opening of 2, 3??Benzofuran− A Two??Step Synthesis of 2H??Chromenes Including Deoxycordiachromene

M Yus, F Foubelo, JV Ferrández

文献索引：Yus, Miguel; Foubelo, Francisco; Ferrandez, Jose V. European Journal of Organic Chemistry, 2001 , # 15 p. 2809 - 2813

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被引用次数: 17

摘要

Abstract The reaction of 2, 3-benzofuran (1) with lithium and a catalytic amount of 4, 4′-di- tert-butylbiphenyl (TDBB, 5 mol%) in THF at 0 C leads to the stereoselective ring opening of the heterocycle, yielding the (Z)-organolithium derivatives (2) which, by reaction with different electrophiles [H 2 O, D 2 O, tBuCHO, PhCHO, Ph (CH 2) 2 CHO, Me 2 CO, nPrCOMe, PhCOMe,(CH 2) 4 CO] at− 78 C and final hydrolysis with water, give the ...