Zhong’an, China
Zhong’an, China

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Lemaire S.,Janssen Pharmaceutical | Houpis I.N.,Janssen Pharmaceutical | Xiao T.,WuxiApptec | Li J.,WuxiApptec | And 8 more authors.
Organic Letters | Year: 2012

A general, transition-metal-free, highly stereoselective cross-coupling reaction between glycosyl bromides and various arylzinc reagents leading to β-arylated glycosides is reported. The stereoselectivity of the reaction is explained by invoking anchimeric assistance via a bicyclic intermediate. Stereochemical probes confirm the participation of the 2-pivaloyloxy group. Finally, this new method was applied to a short and efficient stereoselective synthesis of Dapagliflozin and Canagliflozin. © 2012 American Chemical Society.


Houpis I.N.,Janssen Pharmaceutical | Weerts K.,Janssen Pharmaceutical | Nettekoven U.,Solvias A.G. | Canters M.,Janssen Pharmaceutical | And 3 more authors.
Advanced Synthesis and Catalysis | Year: 2011

The carboxylate anion has been used as a directing group in the aromatic amination of electronically equivalent aryl bromides to afford selective ortho-substituted derivatives (> 99:1 selectivity; 60-80% yield) in the case of copper(I) catalysis. The solvent, base and equivalents of base were important factors in the success of this reaction. Complementary selectivity was achieved with palladium catalysis where the para-substituted derivatives were produced selectively (> 99% selectivity, 70-80% yield). © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.

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