5 years ago

Catalyst-Controlled Stereoselective O-Glycosylation: Pd(0) vs Pd(II)

Catalyst-Controlled Stereoselective O-Glycosylation: Pd(0) vs Pd(II)
Kim Le Mai Hoang, Wei-Lin Leng, Jingxi He, Shasha Zhang, Hui Yao, Xue-Wei Liu, Min-Li Leow, Hongze Liao, Shaohua Xiang
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 yields up to 95% under mild conditions. With Pd(II) catalyst coordination of this glycal donor from the β-face directed by carbonate group, hard nucleophiles (aliphatic alcohols) gave β-glycosides and α-glycosides were obtained from soft nucleophiles (phenols). In contrast, with the Pd(0) catalyst coordinating the donor from the β-face due to steric effect, both hard and soft acceptors could only generate β-glycosides via hydrogen-bond-mediated aglycone delivery.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b01630

DOI: 10.1021/acscatal.7b01630

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