Reaction of Dimethoxycarbene−DMAD Zwitterion with 1,2-Diones and Anhydrides:  A Novel Synthesis of Highly Substituted Dihydrofurans and Spirodihydrofurans

The zwitterion formed by the reaction of dimethoxycarbene and DMAD adds efficiently to one of the carbonyl groups of 1,2-dicarbonyl compounds and anhydrides to generate dihydrofurans and spirodihydrofurans in good yields. In many cases, the carbene inserts into the C−C bond of the dione to yield mas...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-03, Vol.71 (6), p.2313-2319
Main Authors: Nair, Vijay, Deepthi, Ani, Poonoth, Manojkumar, Santhamma, Bindu, Vellalath, Sreekumar, Babu, Beneesh Pattoorpady, Mohan, Resmi, Suresh, Eringathodi
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Anhydrides - chemistry
Chemistry
Exact sciences and technology
Furans - chemical synthesis
Furans - chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Hydrocarbons - chemistry
Ketones - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:The zwitterion formed by the reaction of dimethoxycarbene and DMAD adds efficiently to one of the carbonyl groups of 1,2-dicarbonyl compounds and anhydrides to generate dihydrofurans and spirodihydrofurans in good yields. In many cases, the carbene inserts into the C−C bond of the dione to yield masked vicinal tricarbonyl systems.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo052429k