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Synthesis 2003(9): 1446-1456
DOI: 10.1055/s-2003-40192
DOI: 10.1055/s-2003-40192
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York
Novel Dipolar Cycloaddition Reactions of Zwitterionic Species Generated from Dimethoxycarbene and Dimethyl Acetylenedicarboxylate with Carbonyl Compounds: Facile Synthesis of Dihydrofuran Derivatives
Further Information
Received
30 April 2003
Publication Date:
24 June 2003 (online)
Publication History
Publication Date:
24 June 2003 (online)

Abstract
The reaction of 1:1 zwitterionic species, generated in situ by the addition of dimethoxycarbene to dimethyl acetylenedicarboxylate, towards carbonyl compounds is described. The reactions presented offer a one-pot synthesis of dihydrofuran and spiro dihydrofuran derivatives in high yields.
Key words
aldehydes - carbenes - nucleophilic additions - ketones - quinones
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References
1,3-dipolar cycloaddition has developed as a reaction of prime importance in organic chemistry largely due to the monumental efforts of Huisgen. In view of this, we propose that this reaction be called Huisgen reaction. This recognition, in our opinion, is long overdue.