Direct Syntheses of Spiro- and Fused-Hydrofurans by a Tunable Tandem Semipinacol Rearrangement/Oxa-Michael Addition Protocol

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‐po...

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Bibliographic Details
Published in:Chemistry : a European journal 2013-04, Vol.19 (17), p.5246-5249
Main Authors: Li, Bao-Sheng, Liu, Wen-Xing, Zhang, Qing-Wei, Wang, Shao-Hua, Zhang, Fu-Min, Zhang, Shu-Yu, Tu, Yong-Qiang, Cao, Xiao-Ping
Format: Article
Language:English
Subjects:
Cascade chemical reactions
Chemistry
chemoselectivity
Cyclohexenes - chemistry
Derivatives
Dienes
dihydrofurans
Furans
Furans - chemical synthesis
Furans - chemistry
Methodology
Michael addition
Molecular Structure
semipinacol rearrangements
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
tandem reactions
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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201300205