Highly enantioselective catalytic hydrogenation of a 5-amino-3,5-dioxopentanoic ester

Tetrahedron Letters

Volumn 49, Issue 33, 2008, Pages 4836-4839

  Andrushko, Vasyl ^a   Andrushko, Natalia ^a   König, Gerd ^b   Börner, Armin ^a,c  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^b ratiopharm GmbH   (Germany)

^c UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5 AMINO 3,5 DIOXOPENTANOIC ESTER; ESTER DERIVATIVE; LIGAND; PHOSPHINE; VALERIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; HYDROGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 46049084988     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.018     Document Type: Article

References (17)

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11. 3), 3.48 (br s, 1H, OH), 4.38-450 (m, 1H, CHOH).
12. 2, EtOH, i-PrOH or ethyl acetate.
13. 2-pressure of 25 bar in comparison with the reaction at 25 °C, but still above 85% ee.
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16. binol,S)-13, respectively. The enantiomeric excess of alcohol 4 was calculated from the integral intensities of the peaks.
17. 24 +1.7 (c 8.0, MeOH) of product 4, which was prepared by hydrogenation of carbonyl compound 3 using [Ru((S)-BINAP)(p-cymene)Cl]Cl complex as pre-catalyst at 5 bar of initial hydrogen pressure and obtained with an enantioselectivity of 96% ee (Table 1, entry 26).