19348-63-1Relevant articles and documents
Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor
Watson, Andrew J.A.,Wakeham, Russell J.,Maxwell, Aoife C.,Williams, Jonathan M.J.
supporting information, p. 3683 - 3690 (2014/05/20)
A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.
Glycono-1,3-lactams, Xylo Series: Stereoselective Access by Cycloaddition, Exploratory Transformations, and Discovery of a New, Highly Selective Inhibitor of Glucoamylases
Kraemer, Bernd,Franz, Thomas,Picasso, Sylviane,Pruschek, Petra,Jaeger, Volker
, p. 295 - 297 (2007/10/03)
Cycloaddition of chiral imines 4-7, derived from 2-O-benzylglyceraldehyde, with α-alkoxy ketenes 1-3 furnished 3-amino-3-deoxy-glycono-1,3-lactams 8-15 (50-78 percent) with 2,3-cis configuration in diastereomeric ratios of 87 : 13 to > 95 : 5.From these O,N-deprotected β-lactams 16-18 were prepared.Reduction of the xylono-1,3-lactam 18 using monochloroalane (ClAlH2) produced the corresponding azetidine 19, while reduction of 14 with LiAlH4 gave the aminotetrol derivative 20.Treatment of the β-lactam triol 21 with NaIO4 led to the 3,4-dihydro-2H-1,4-oxazine-3-one 22, via cleavage of the C2-C3 bond and recyclization.The 1,3-imino-xylitol 19 exhibited highly selective inhibition of the two gluco-amylases tested (IC50 values of 31 and 4 (M)).
