Highly Diastereoselective Synthesis of
Lisi Yuan1, Ya Fang1, Zhaobo Zhou1
1State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.
Abstract:
This Letter presents a highly diastereoselective synthesis of C-hydroxymethine glycosides from glycal anomers using a chiral N-heterocyclic carbene-copper catalyst. The high diastereoselectivity was synergistically controlled by the stereocenter of the substrate and chirality of the N-heterocyclic carbene-copper complex without being interrupted by the stereochemistry of C5 and the anomeric position. This approach enables the production of a diverse array of C-hydroxymethine glycosides using synthetically versatile glycals and various functionalized aldehydes.
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