posted on 2021-12-27, 18:35authored bySteven Truong, David R. Mootoo
The
stereoselective synthesis of E- and Z- isomers of a C- mannosyl crotylpinacolboronate via Ni-promoted reactions
on an allylic acetate and a diene precursor, respectively, is described.
The E- and Z- isomers reacted with
1,2-O-isopropylidene glyceraldehyde in the presence
or absence of (R)- and (S)- TRIP
catalysts, to give predominantly 3,4-anti and 3,4-syn crotylation products, respectively, with moderate to
high facial selectivity. These products were transformed to biologically
relevant C-manno-disaccharides.