Tetrahedron

New aspects in the synthesis of mono-and dialkylfurans

I Bock, H Bornowski, A Ranft, H Theis

Index: Bock, Inge; Bornowski, Hans; Ranft, Andreas; Theis, Heinz Tetrahedron, 1990 , vol. 46, # 4 p. 1199 - 1210

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Citation Number: 64

Abstract

3-substituted furan systems can be obtained by alkylation of 3-lithium furans with various electrophiles in the presence of hexamethylphosphoric acid triamide in good yields. The 2- or 5-position of 3-methyl furan is blocked with high regioselectivity by silylation. After metalation and alkylation of the remaining free α-position and subsequent desilylation the 2, 3-and 2, 4-disubstituted furans are obtained. These methods are used to synthesize the ...