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Chemoselective 1,3-dipolar cycloadditions of azomethine ylide with conjugated dienes

✍ Scribed by Laura C. Blumberg; Brian Costa; Rebecca Goldstein

Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
328 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

Methods are described of synthesizing various 3-carboxy-4-vinyl pyrrolidines, versatile building blocks for our drug discovery efforts. The 1,3-dipolar cycloaddition between activated olefins and nonstabilized azomethine ylide is a known method for synthesizing pyrrolidines in a stereospecific manner. Steric and electronic effects on the chemoselectivity of the 1,3-dipolar cycloaddition between azomethine ylide and a,b,c,d-unsaturated carboxylates have been explored.

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✍ Jiří Dostál; Milan Potáček; Otakar Humpa; JaromÍR Marek 📂 Article 📅 2010 🏛 Wiley (John Wiley & Sons) ⚖ 399 KB 👁 1 views

## Abstract Azomethine ylides generated from 5‐(alkoxycarbonylmethyl)phenanthridinium cations were studied in 1,3‐dipolar cycloadditions with dimethyl maleate and dimethyl fumarate as dipolarophiles. The cycloadducts with the pyrrolidino[1,2‐f]phenanthridine skeleton easily underwent dehydrogenatio