A chiral bidentate phosphoramidite (Me-BIPAM) for Rh-catalyzed asymmetric hydrogenation of α-dehydroamino esters, enamides, and dimethyl itaconate

doi:10.1016/j.tetlet.2008.12.086

Tetrahedron Letters

Volume 50, Issue 26, 1 July 2009, Pages 3158-3160

https://doi.org/10.1016/j.tetlet.2008.12.086 Get rights and content

Abstract

High performance of Me-BIPAM for enantioselective hydrogenation of α-dehydroamino esters, enamides, and dimethyl itaconate was demonstrated. [Rh(Me-BIPAM)(diene)]X (diene = cod, nbd; X = BF₄, PF₆, SbF₆) gave optically active β-aryl α-amino esters up to 99% ee, 1-arylethylamines up to 97% ee, methyl 2-acetylaminobutanoate with 90% ee, and dimethyl 2-methylsuccinate with 97% ee under 0.3−0.8 MPa dihydrogen with 0.1−1 mol % catalyst loading.

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Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research in Priority Areas (No. 18064001, Synergy of Elements) and the Global COE Program (No. B01, Catalysis as the Basis for Innovation in Materials Science) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

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A chiral bidentate phosphoramidite (Me-BIPAM) for Rh-catalyzed asymmetric hydrogenation of α-dehydroamino esters, enamides, and dimethyl itaconate

Abstract

Graphical abstract

Section snippets

Acknowledgments

Acc. Chem. Res.

Chem. Soc. Rev.

Tetrahedron: Asymmetry

Org. Biomol. Chem.

Org. Biomol. Chem.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

Angew. Chem., Int. Ed.

Tetrahedron: Asymmetry

J. Am. Chem. Soc.

Tetrahedron Lett.

Adv. Synth. Catal.

J. Am. Chem. Soc.

J. Org. Chem.

Tetrahedron: Asymmetry

Tetrahedron: Asymmetry

Angew. Chem., Int. Ed.

Chem. Commun.

Org. Lett.