Furanoside diphosphite

Fig. 14 Summary of the best results obtained in the Ir-catalyzed hydrogenation using nanoparticles stabilized with furanoside diphosphite ligands 14 and 15...

Dieguez, M., Ruiz, A., Claver, C. Tunable furanoside diphosphite ligands a powerful approach in asynunetric catalysis. Dalton Trans. 2003, (15), 2957-2963. 

Another successful family of ligands is the sugar-based furanoside ligands 4, 19-23 (Fig. 5) [21-23,43,50]. The modular construction of these ligands allows to fine tune (a) the different configurations of the carbohydrate backbone and (b) the steric and electronic properties of the diphosphite substituents. They show excellent enantioselectivity on both the S and R enantiomer of the product (up to 93%) and excellent regioselectivity (up to 98.8%) under mild conditions (Table 2). 

As represented in Equation (122), a rhodium-catalyzed hydroformylation of 2,3- and 2,5-dihydrofuran using furanoside-derived chiral diphosphite ligands, for example, 237, provided 3-formyltetrahydrofuran as the major product with ee up to 75% <2005CC1221>. 

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