Titanium‐Catalyzed Diastereoselective Keto‐ and Iminonitrile Cyclizations
Abstract
Substituted five-membered carbocycles with multiple stereocenters are common structural motifs of natural products but difficult to synthesize in a stereoselective fashion. In this study, we report a titanium(III)-catalyzed diastereoselective cyclization of keto- and iminonitriles that forms oxygenated and aminated cyclopentanones in good yield and diastereoselectivity. The derivatization into cyclopentyls with three consecutive stereocenters and a cyclopentenone is demonstrated. With support by DFT calculations, a transition state model is derived that is in agreement with an earlier proposal for related ketomalononitrile cyclizations.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Cyclopropane Reaction Mechanisms
Synthetic Organic Chemistry Methods
Publication details
- Journal / source
- Chemistry - A European Journal
- Publisher
- Wiley
- Volume
- 32
- Issue
- 35
- Pages
- e71206–e71206
- Publication date
- 6 June 2026
- Language
- EN