Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands

Journal of Organic Chemistry

Volumn 71, Issue 5, 2006, Pages 2026-2036

  Panella, Lavinia ^a   Aleixandre, Alicia Marco ^a   Kruidhof, Gerlof J ^a   Robertus, Jort ^a   Feringa, Ben L ^a   De Vries, Johannes G ^a,b   Minnaard, Adriaan J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL LIGANDS; HECK REACTION; HYDROGEN PRESSURE; MULTIGRAM SCALE;

CATALYSIS; CONDENSATION; HYDROGENATION; ORGANIC SOLVENTS; RHODIUM; SYNTHESIS (CHEMICAL);

ESTERS;

ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; AMINE; CYCLOHEXANONE; ESTER DERIVATIVE; FORMAMIDE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; LIGAND; PHOSPHORAMIDOUS ACID DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HECK REACTION; HYDROGENATION; POLYMERIZATION; PRESSURE; REACTION ANALYSIS; SYNTHESIS;

ACRYLATES; ALDEHYDES; AMINO ACIDS; CATALYSIS; CINNAMATES; ESTERS; FORMAMIDES; HYDROGENATION; LIGANDS; ORGANOPHOSPHORUS COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 33644659716     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052451d     Document Type: Article

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140. Prepared with pyruvic acid and formamide in 16% yield according to a literature procedure: Frankel, M.; Reichmann, M. E. J. Chem. Soc. 1952, 105, 289.
141. This allowed comparison with results previously obtained for 2-acetamidoacrylic acid (ref 11b).
142. Prepared from commercially available (L)-phenylalanine methyl ester hydrochloric salt (ref 28a).
143. No reaction was observed applying the same conditions to the N-acyl protected amino ester.
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152. Data in agreement with literature: ref 46a.
153. Data in agreement with literature: Roos, E. C.; Lopez, M. C.; Brook. M. A.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B.; Kamphuis J.; Schoemaker, H. E. J. Org. Chem. 1993, 58, 3259.
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