A One-Pot Synthesis of Doubly Unsaturated Trifluoromethyl Amines: Easy Access to CF3-Substituted Piperidines.

✍ Scribed by Guillaume Magueur; Julien Legros; Franck Meyer; Michele Ourevitch; Benoit Crousse; Daniele Bonnet-Delpon

• Publisher: John Wiley and Sons
• Year: 2005
• Weight: 37 KB
• Volume: 36
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.200532142

✦ Synopsis

Pyridine derivatives R 0380

A One-Pot Synthesis of Doubly Unsaturated Trifluoromethyl Amines: Easy Access to CF3-Substituted Piperidines. -Starting from acetaldimines (I), double allylation can be performed in one pot by use of activated zinc. In some cases, the addition of stoichiometric or catalytic amounts of CuI improves the yields. Subsequent ring-closing metathesis reaction of the resulting amines gives the desired piperidines. Under Pauson-Khand conditions these amines are converted into heterobicyclic compounds. An efficient asymmetric version is also performed providing the products with excellent diastereoselectivity. -(MAGUEUR, G.;