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Communication | Special issue | Vol 72, No. 1, 2007, pp.127-132
Published online, 22nd December, 2006
DOI: 10.3987/COM-06-S(K)23
Diastereoselective Reduction of α-Imino Esters with Tris(trimethylsilyl)aluminum

Makoto Shimizu,* Yasuki Niwa, Takeshi Nagai, and Iwao Hachiya

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


Tris(trimethylsilyl)aluminum was found to be a good chemoselective reducing reagent for α-imino esters to give α-amino esters in good yields. Application to the reduction of 3,5-disubstituted 5,6-dihyro-2H-1,4-oxazine-2-ones realized a stereoselective conversion into cis-3,5-disubstituted morpholine-2-ones.