An efficient 1,2-chelation-controlled reduction of protected hydroxy ketones via Red-Al.
In this paper, we have demonstrated that Red-Al is an efficient chelation-controlled reducing reagent for acyclic acetal (i.e., MOM, MEM, SEM, and BOM) protected alpha-hydroxy ketones. Typically, diastereomeric ratios (dr) ranged from 5 to 20:1 for the 1,2- anti-diols in good to excellent yields.
Bajwa
Naval
N
Department of Chemistry, 250 Hackberry Lane, The University of Alabama, Tuscaloosa, Alabama 35487-0336, USA.
Jennings
Michael P
MP
D002614:Chelating Agents / Q000737:chemistry*; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
D002614:Chelating Agents; D007659:Ketones; D009942:Organometallic Compounds; C007396:dihydrobis(2-methoxyethoxy)aluminate