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ChemInform Abstract: Regio- and Stereoselective Synthesis of γ-Alkylidenebutenolides by Cyclization of Dilithiated 1,3-Dicarbonyl Compounds with N,N′-Dimethoxy-N,N′-dimethylethanediamide.

✍ Scribed by Peter Langer; Martin Stoll

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Regio-and Stereoselective Synthesis of γ-Alkylidenebutenolides by Cyclization of Dilithiated 1,3-Dicarbonyl Compounds with N,N'-Dimethoxy-N,N'-dimethylethanediamide.

-A new and convenient method for the selective preparation of functionalized γ-alkylidenebutenolides, intermediates for natural product synthesis, is developed. This method provides the first examples for cyclization reactions of 1,3-dicarbonyl compounds with oxalic acid derived dielectrophiles which proceed by attack of a terminal carbon atom of the nucleophile.

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Regio- and Stereoselective Synthesis of
Regio- and Stereoselective Synthesis of γ-Alkylidenebutenolides by Cyclization of Dilithiated 1,3-Dicarbonyl Compounds with N,N′-Dimethoxy-N,N′-dimethylethane- diamide
✍ Peter Langer; Martin Stoll 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 90 KB 👁 1 views

The remarkably simple synthesis of γ-alkylidenebutenolides 3 is achieved by cyclization of the dilithiated 1,3-dicarbonyl compounds 1 with N,N'-dimethoxy-N,N'-dimethylethanediamide (2). This regio- and stereoselective cyclization provides a route to a wide range of butenolides, which are of pharmaco