Synthesis of 3-halo-2,5-disubstituted furans via CuX mediated cyclization-halogenation reactions

Authors

Arife Yazici, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow

RIS ID

38449

Publication Details

Yazici, A. and Pyne, S. G. (2011). Synthesis of 3-halo-2,5-disubstituted furans via CuX mediated cyclization-halogenation reactions. Tetrahedron Letters, 52 (12), 1398-1400.

Abstract

The Cu(I) halide (X = I, Br, Cl) mediated reactions of Cbz-protected cis-2-phenylethenyl-3-hydroxypyrrolidine gave novel 3-halo-2,5-trisubstituted furans in good yields, via a cyclization-halogenation, ring-opening reaction sequence. In contrast, the reactions with CuCN gave mainly the corresponding 3-cyanofuro[3,2-b]pyrrole formed from a cyclization-cyanation reaction.