A synergistic Rh(I)/organoboron-catalysed site-selective carbohydrate functionalization that involves multiple stereocontrol

Rao VUB, Wang C, Demarque DP, Grassin C, Otte F, Merten C, Strohmann C, Loh CCJ (2022)

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Dr. Uday Vipilli Bhaskara Rao and Caiming Wang from the Loh research group lately reported a synergistic chiral Rh(I) and organoboron catalyzed site-selective carbohydrate functionalization strategy, which enabled unprecedented access into synthetically challenging but biologically relevant aryl naphthalene glycosides.

Exquisite multiple aspects of stereocontrol, including enantio-, diastereo-, regio-, anomeric control and dynamic kinetic resolution were found to be concomitantly operative, uncovered by means of mechanistic studies and DFT calculations. In successful collaboration with Christian Merten’s group and Carsten Strohmann’s group from the Ruhr University of Bochum and the Technical University of Dortmund respectively, the challenging absolute structural elucidation of various regioisomers and diastereomers were achieved by means of vibrational circular dichroism (VCD) and single crystal X-ray analysis.