Regioselective Synthesis of Functionalized Biaryls Based on the First [3+ 3] Cyclocondensations of 4-Aryl-1, 3-bis (trimethylsilyloxy) buta-1, 3-dienes

…, A Villinger, H Reinke, C Fischer, P Langer

Index: Adeel, Muhammad; Rashid, Muhammad A.; Rasool, Nasir; Ahmad, Rasheed; Villinger, Alexander; Reinke, Helmut; Fischer, Christine; Langer, Peter Synthesis, 2009 , # 2 p. 243 - 250

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Citation Number: 4

Abstract

The 4-arylacetoacetates 2a-e were prepared by lithium diisopropylamide mediated reaction of methyl acetate with the arylacetyl chlorides 1a-e (Scheme 1, Table [¹] ). The silylation of 2a-e afforded the 3-(silyloxy)-2-en-1-ones 3a-e. The novel 4-aryl-1,3-bis(silyloxy)-1,3-dienes 4a-e were prepared by deprotonation (LDA) of 3a-e at -78 ˚C and subsequent addition of chlorotrimethylsilane. The trimethylsilyl triflate catalyzed cyclization of 4-aryl-1,3-bis( ...