89359-07-9Relevant academic research and scientific papers
Asymmetric Synthesis. Part 6. Copper Salt promoted Grignard Reagent Additions to Ethyl 2,3-Dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate and subsequent Formation of Optically Active 2-Alkyl (or Aryl) Butane-1,4-dioic Acids and Butyro-1,4-lactones
Lawston, Ian W.,Inch, Thomas D.
, p. 2629 - 2635 (2007/10/02)
The copper-salt promoted 1,4-additions of aryl and t-butyl Grignard reagents to ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate are highly stereoselective yielding products with the D-manno-configuration.In contrast isopropyl and ethyl Grignarg reagents give products preponderantly with the D-gluco-configuration.Cyclohexylmagnesium bromide does not react stereoselectively but gives a 55:45 mixture of the D-gluco- and D-manno-isomers.Controlled degradation of the carbohydrate molecule affords 2-aryl (alkyl) butane-1,4-dioic acids and 3-aryl (alkyl)-butyro-1,4-lactones.The enantiomeric purity of these products is established by reference to known products or by use of optically active n.m.r. shift reagents.
