Journal
ORGANIC LETTERS
Volume 11, Issue 7, Pages 1527-1530Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900126q
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- NIH [R 15 GM081889-03]
- HHMI
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In the Rh-2(OAC)(4)-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 40 and 60 protecting groups. Acyclic protection permits high alpha-anomer selectivity with further improvement in less polar solvents, while electron-withdrawing protecting groups limit C3-oxidized byproducts. Stereocontrol and bifurcation between alkene insertion and C3-H oxidation reflect an interplay of conformational, stereoelectronic, and inductive factors.
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