SYNTHESIS OF A NEW CHIRAL BIS-ARSINE LIGAND BASED ON NATURAL CARBOHYDRATES

SOL C. PARAJÓN PUENZO; JOAQUIN ARATA BADANO; MARTIN LOPEZ VIDAL; OSCAR VARELA; SANDRA E. MARTÍN

CAMPOS DO JORDAO

Congreso; 15th BMOS - Brazilian Meeting on Organic Synthesis; 2013

UNIVERSIDAD DE SAO PAULO

Transition-metal-catalyzed asymmetric allylic substitutions have become one of the most powerful tools for asymmetric C−C bond formation.1 Chiral diphosphine ligands have been some of the largest classes of ligands used in asymmetric substitutions. Trost developed the chiral ligand 1 (Fig. 1), which played a crucial role in the improvement of Pdcatalyzed asymmetric substitutions.2 Based on the Trost modular ligand (TML) system 3 (Fig. 1) a family of ligands has been prepared. We recently reported the synthesis and application of the novel chiral bis-arsine ligand 2 derived from TML.3 Figure 1. Phosphine and arsine Trost modular ligands. Currently, significant attention has been turned towards the use of chiral ligands based on natural carbohydrates.4 Herein, we describe the synthesis of a chiral bis-arsine ligand such as 2 containing the chiral scaffold derived from a carbohydrate