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2,2',5,5'-tetramethyl-4,4'-bis(diphenylphoshino)-3,3'-bithiophene: A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis

2,2',5,5'-tetramethyl-4,4'-bis(diphenylphoshino)-3,3'-bithiophene: A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis

T Benincori, E Cesarotti, O Piccolo, F Sannicolo

J Org Chem. 2000 Apr 7;65(7):2043-7.

PMID: 10774024

Abstract:

The four-step straightforward synthesis of enantiopure (+)- and (-)-2,2',5,5'-tetramethyl-4,4'-bis-(diphenylphoshino)-3,3'-bithiophene (tetraMe-BITIOP), a new C2-symmetry chelating ligand for transition metals, is described, starting from 2,5-dimethylthiophene. The complexes of this electron-rich diphosphine with Ru(II) and Rh(I) were used as catalysts in some homogeneous hydrogenation reactions of prostereogenic carbonyl functions of alpha- and beta-ketoesters, of prostereogenic carbon-carbon double bonds of substituted acrylic acids, and of N-acetylenamino acids. The enantiomeric excesses were found to be excellent in all the experiments and comparable with the best results reported in the literature for the same reactions, carried out under similar experimental conditions, with the metal complexes of the most popular chiral diphosphine ligands as catalysts.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2404899	2,3′-Bithiophene		2404-89-9	Price

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