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Communication | Special issue | Vol 74, No. 1, 2007, pp.177-183
Published online, 4th October, 2007
DOI: 10.3987/COM-07-S(W)43
Titanium Tetraiodide Promoted Reductive Opening of 2-(1-Benzyloxyiminoethyl)aziridines, Leading to Aza-Aldol Reaction

Makoto Shimizu,* Shuji Nishiura, and Iwao Hachiya

*Department of Chemistry for Materials, Faculty of Engineering, Mie University, 1577 Tsu, Mie 514-8507, Japan


Reductive ring-opening of 2-(1-benzyloxyiminoethyl)aziridines was regioselectively carried out with titanium tetraiodide to form the titanium aza-enolates, which in turn were subjected to addition reaction with aldehydes to give aza-aldol products in good yields with high diastereoselectivities.