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Direct Syntheses of Spiro‐ and Fused‐Hydrofurans by a Tunable Tandem Semipinacol Rearrangement/Oxa‐Michael Addition Protocol
Author(s) -
Li BaoSheng,
Liu WenXing,
Zhang QingWei,
Wang ShaoHua,
Zhang FuMin,
Zhang ShuYu,
Tu YongQiang,
Cao XiaoPing
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300205
Subject(s) - tandem , michael reaction , combinatorial chemistry , computer science , scheme (mathematics) , sequence (biology) , protocol (science) , furan , chemistry , organic chemistry , mathematics , engineering , medicine , mathematical analysis , biochemistry , alternative medicine , catalysis , pathology , aerospace engineering
A highly chemoselective one‐pot reaction has been developed involving a tandem semipinacol rearrangement/oxa‐Michael addition sequence in which the in situ generated ketol diene intermediate can be transformed specifically to either the spiro‐ or fused‐dihydrofuran products (see scheme). This one‐pot tandem reaction represents a general synthetic methodology for the syntheses of the two different kinds of furan derivatives.