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Simple and versatile synthesis of 1-pyrroline derivatives through thermal rearrangement of N-cyclopropylimines

✍ Scribed by Pedro J. Campos; Alberto Soldevilla; Diego Sampedro; Miguel A. Rodrı́guez


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
121 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


N-Cyclopropylimines rearrange under thermal conditions to give 1-pyrrolines. The effect of imine and cyclopropane substitution is explored. This methodology allows the presence of different substituents (alkyl, alkenyl, aryl) and the reaction proceeds regiospecifically.


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Synthesis of (R)- and (S)-3-(tert-butyld
✍ Shun-Ichi Murahashi; Hiroaki Ohtake; Yasushi Imada 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 147 KB

## Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)- 2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-l-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone