ChemInform Abstract: A New Versatile Reagent for the Synthesis of Cyclopropylamines Including 4-Azaspiro(2.n)alkanes and Bicyclo(n.1.0)alkylamines.

✍ Scribed by V. CHAPLINSKI; H. WINSEL; M. KORDES; A. DE MEIJERE

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199723088

✦ Synopsis

A New Versatile Reagent for the Synthesis of Cyclopropylamines Including 4-Azaspiro(2.n)alkanes and Bicyclo(n.1.0)alkylamines.

-The reaction of dialkylcarboxamides or the ester (IV) with equimolar ratios of Grignard reagents and methyltriisopropyloxytitanium gives cyclopropane derivatives in better yields than the previously reported reaction in the presence of Ti(OiPr)4. Application of the reaction to the ω-bromo amide (X) with in situ generation of the Grignard compound provides the bicyclic compound (XI). Furthermore, the N-alkylated lactam (XIII) is converted to the spiro products (XV) with only small amounts of by-product (XVI). -(CHAPLINSKI, V.;