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Communication | Special issue | Vol 70, No. 1, 2006, pp.57-64
Published online, 25th July, 2006
DOI: 10.3987/COM-06-S(W)9
Titanium Tetraiodide Mediated Reductive Opening of Aziridines, Leading to the Aldol and Mannich-Type Reactions

Makoto Shimizu,* Hiroshi Kurokawa, Shuji Nishiura, and Iwao Hachiya

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

Abstract

Reductive ring-opening of N-tosylazirindes was readily carried out with titanium tetraiodide to form the titanium enolates, which in turn were subjected to addition reaction with aldehydes or imines to give aldol or Mannich-type products in good yields.