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Synthesis of 2-azabicyclo[3.3.1]nonanes by means of (carbamoyl)dichloromethyl radical cyclization

✍ Scribed by Josefina Quirante; Carmen Escolano; Mireia Massot; Josep Bonjoch

Book ID
104207428
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
852 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

A new procedure for the synthesis of 2-azabicyclo[3.3.1 ]nonanes by intramolecular carboradical cyclization of 4-(trichloroacetamido)cyclohexenes substituted with an electron withdrawing substituent (ester or nitrile) is described. The procedure allows the preparation of synthetically interesting azabicyclos 14 and 15 in nearly 70% yield.

πŸ“œ SIMILAR VOLUMES

Cyclization of 1-(carbamoyl)dichlorometh
Cyclization of 1-(carbamoyl)dichloromethyl radicals upon activated alkenes. A new entry to 2-azabicyclo[3.3.1]nonanes
✍ Josefina Quirante; Carmen Escolano; Laura CostejΓ ; Josep Bonjoch πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 239 KB

The synthesis of 2-azabicyclo[3.3.1]nonanes using a radical cyclization process as the piperidine ring-forming step is described. The reaction involves 1-(carbamoyl)dichloromethyl radicals which react inlramolecularly with simple or activated alkenas, such as enol acetates or silyl enol ethers.