Stereoselective Organocatalytic Fucosylation with Isothioureas
Charles Enlow1, Riley N Brown1, Trevor E Hoodenpyle1
1Department of Chemistry, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, United States.
None:
This letter describes a catalytic, α-selective glycosylation of fucosyl chloride donors mediated by a nucleophilic thiourea. This reaction is highly selective in forming both α-fucosyl and α-2-deoxy-2-azido-fucosylated glycosides, including sterically encumbered linkages. Both conformationally flexible and constrained donors participate, giving good to complete α selectivity without the need for directing groups or temperature control. Additionally, we have utilized the parent reaction to access a generalized intermediate for the synthesis of fucosyl lipids.
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