Highly enantioselective rhodium-catalyzed hydrogenation of β-dehydroamino acid derivatives using monodentate phosphoramidites

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14552-14553

  Peña, Diego ^a   Minnaard, Adriaan J ^a   De Vries, Johannes G ^a,b   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; LIGAND; PHOSPHORAMIDIC ACID DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

AMINO ACIDS; CATALYSIS; HYDROGENATION; ORGANOPHOSPHORUS COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 0037065328     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028235t     Document Type: Article

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38. 2.
39. Although the diastereoisomer (S,S)-3 seems to be less stable than (S,R)-3, both led to a similar ee. This result is analogous to one reported by Reetz and Mehler in the case of monophosphites (see ref 5d).
40. It is known that polar solvents favor the hydrogenation of -β-(acylamino)acrylates probably because these solvents can break up the intramolecular hydrogen bond in the substrate and thus allow a selective bidentate coordination to the metal (see ref 9a and f).
41. Interestingly, it has been reported that in the case of bidentate phosphines, the ee decreases upon increasing the pressure (see ref 9a and c).