4.4 Article

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

Journal

TETRAHEDRON LETTERS
Volume 50, Issue 26, Pages 3158-3160

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.12.086

Keywords

Bidentate phosphoramidite ligand; Rhodium catalyst; Asymmetric hydrogenation

Funding

  1. Grant-in-Aid for Scientific Research in Priority Areas [18064001]
  2. Ministry of Education, Culture, Sports, Science, and Technology, Japan [B01]
  3. Grants-in-Aid for Scientific Research [18064001] Funding Source: KAKEN

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High performance of Me-BIPAM for enantioselective hydrogenation of alpha-dehydroamino esters, enamides, and dimethyl itaconate was demonstrated. [Rh(Me-BIPAM)(diene)]X (diene = cod, nbd; X = BF4, PF6, SbF6) gave optically active beta-aryl alpha-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. (C) 2009 Elsevier Ltd. All rights reserved.

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