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

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

Puenzo, Sol C. Parajón; Badano, Joaquín Arata; Vidal, Martin G. Lopez; Varela, Oscar; Martín, Sandra E.

Abstract:

Transition-metal-catalyzed asymmetric allylic substitutions have become one of the most powerful tools for asymmetric C−C bond formation. 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 Pd-catalyzed asymmetric substitutions. 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. Currently, significant attention has been turned towards the use of chiral ligands based on natural carbohydrates. Herein, we describe the synthesis of a chiral bis-arsine ligand such as 2 containing the chiral scaffold derived from a carbohydrate.

Transition-metal-catalyzed asymmetric allylic substitutions have become one of the most powerful tools for asymmetric C−C bond formation. 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 Pd-catalyzed asymmetric substitutions. 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. Currently, significant attention has been turned towards the use of chiral ligands based on natural carbohydrates. Herein, we describe the synthesis of a chiral bis-arsine ligand such as 2 containing the chiral scaffold derived from a carbohydrate.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013102155749

Referências bibliográficas

• [1] 1. a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. b) Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 120, 264.
• [2] 2. Butts, C. P.; Filali, E.; Lloyd-Jones, G. C.; Norrby, P.-O.; Sale, D. A.; Schramm, Y.; J. Am. Chem. Soc. 2009, 131, 9945.
• [3] 3. Uberman, P. M.; Caira M. R.; Martín, S. E., Organometallics 2013, 32, 3220.
• [4] 4. a) Dieguez, M.; Claver, C.; Pamies, O. Eur. J. Org. Chem. 2007, 4621. b) Glegola, K.; Johannesen, S.; Thim, L.; Goux-Henry, C.; Skrydstrup, T.; Framey, E.; Tetrahedron Letters. 2008, 49, 6635.

Como citar:

Puenzo, Sol C. Parajón; Badano, Joaquín Arata; Vidal, Martin G. Lopez; Varela, Oscar; Martín, Sandra E.; "SYNTHESIS OF A NEW CHIRAL BIS-ARSINE LIGAND BASED ON NATURAL CARBOHYDRATES", p-136-136. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013102155749