Directed reduction of beta-amino ketones to syn or anti 1,3-amino alcohol derivatives.
[reaction: see text] The reduction of beta-amino ketones with samarium(II) iodide has been investigated. Either the syn or anti 1,3-amino alcohols can be obtained as the major product due to a divergence in selectivity with different N-protecting groups.
Keck
Gary E
GE
Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City 84112-0850, USA. keck@chemistry.utah.edu
Truong
Anh P
AP
D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D001685:Biological Factors / Q000138:chemical synthesis; D006865:Hydrogenation; D007454:Iodides / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012493:Samarium / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D000605:Amino Alcohols; D000900:Anti-Bacterial Agents; D001685:Biological Factors; D007454:Iodides; D007659:Ketones; D012493:Samarium; C409809:samarium diiodide