Intramolecular titanium-mediated aminocyclopropanation of terminal alkenes: easy access to various substituted azabicyclo[n.1.0]alkanes

Gerd-Dieter Tebben; Karsten Rauch; Christian Stratmann; Craig M Williams; Armin de Meijere

doi:10.1021/ol027352q

Intramolecular titanium-mediated aminocyclopropanation of terminal alkenes: easy access to various substituted azabicyclo[n.1.0]alkanes

Org Lett. 2003 Feb 20;5(4):483-5. doi: 10.1021/ol027352q.

Authors

Gerd-Dieter Tebben¹, Karsten Rauch, Christian Stratmann, Craig M Williams, Armin de Meijere

Affiliation

¹ Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany.

PMID: 12583749
DOI: 10.1021/ol027352q

Abstract

[reaction: see text] A variety of substituted azabicyclo[n.1.0]alkanes were synthesized by intramolecular titanium-mediated cyclopropanation of N-benzyl-N-(2-alkylalk-3-enyl)formamides and N-benzyl-N-alkadienylformamides. N-Benzylpyrroline upon treatment with Grignard reagents undergoes a titanium-mediated carbomagnesiation to yield N-benzyl-N-(2-alkylbut-3-enyl)amines.