Tetrahedron letters

Tetramethyldiamido phosphate directed β-lithiation of a π-excessive heterocycle; d 2-synthon to 2-substituted butenolides

JH Näsman, N Kopola, G Pensar

Index: Naesman, Jan H.; Kopola, Nina; Pensar, Goeran Tetrahedron Letters, 1986 , vol. 27, # 12 p. 1391 - 1394

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Citation Number: 31

Abstract

Abstract The tetramethyldiamido phosphate group is described as a novel and tetracoordinated directing group in a reliable and synthetically useful β-lithiation of furan 1. Addition of 1.1 equiv. n-BuLi to 1 and quenching with electrophiles gave 2, 3-disubstituted furans 3. In 98–100% formic acid 3 is converted to 4 in good overall yield. Thus furyltetramethyldiamido phosphate 1 is ad 2-synthon for 2-furanone.