Novel Dipolar Cycloaddition Reactions of Zwitterionic Species Generated from Dimethoxycarbene and Dimethyl Acetylenedicarboxylate with Carbonyl Compounds: Facile Synthesis of Dihydrofuran Derivatives

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

References

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1

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.