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Issue 31, 2013

Chemoselective synthesis of tetrasubstituted furansvia intramolecular Wittig reactions: mechanism and theoretical analysis

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Abstract

An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.

Graphical abstract: Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions: mechanism and theoretical analysis

Supplementary files

Article information


Submitted
26 Apr 2013
Accepted
07 Jun 2013
First published
07 Jun 2013

Org. Biomol. Chem., 2013,11, 5156-5161
Article type
Paper

Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions: mechanism and theoretical analysis

Y. Lee, Y. Lee, C. Lee, C. Sheu, B. Lin, J. Wang and W. Lin, Org. Biomol. Chem., 2013, 11, 5156 DOI: 10.1039/C3OB40858B

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