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Tetramethyldiamido phosphate directed β-lithiation of a π-excessive heterocycle; d2-synthon to 2-substituted butenolides

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
27
Issue
12
Identifiers
DOI: 10.1016/s0040-4039(00)84267-7

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 a d 2-synthon for 2-furanone.

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