Stereoselective construction of various O-glycosidic bonds was first achieved by different palladium sources using 3,4-O-carbonate galactal as the donor to reach up to 95% yield under mild conditions. With Pd(II) catalyst coordination of this glycal donor from β-face directed by carbonate group, hard nucleophiles (aliphatic alcohols) gave β-glycosides and α-glycosides were obtained from soft nucleophiles (phenols). On the contrary, with Pd(0) catalyst coordinating the donor from β-face due to steric effect, both hard and soft acceptors could only generate β-glycosides via hydrogen-bond-mediated aglycone delivery.

Catalyst-controlled stereoselective O-glycosylation: Pd(0) vs Pd(II)

255th National Meeting (2018)

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