Enantioselective hydrogenation of an α-alkoxy substituted ketone with chiral ruthenium (phosphinoferrocenyl)oxazoline complexes

Tetrahedron Asymmetry

Volumn 17, Issue 4, 2006, Pages 550-553

  Tellers, David M ^a   Bio, Matthew ^a   Song, Zhiguo J ^a   McWilliams, J Christopher ^a   Sun, Yongkui ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; KETONE; KETONE DERIVATIVE; OXAZOLINE DERIVATIVE; RUTHENIUM COMPLEX; SOLVENT;

ARTICLE; ASYMMETRIC CATALYSIS; BIOTRANSFORMATION; CATALYST; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; PROCESS OPTIMIZATION; SOLVENT EFFECT; SUBSTITUTION REACTION;

EID: 33645875046     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.12.028     Document Type: Article

References (21)

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17. It should also be noted that the reduction of ketone 1 with borane-diethylaniline complex in the presence of stoichiometric oxazaborolidine (OAB) alcohol, 2 was obtained in 86% ee. See:. Corey E.J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1998) 1986-2012
18. A total of 35 chiral bisphosphine ruthenium catalysts were screened.
19. Various solvents were examined and ethyl acetate was found to give the best enantioselectivity.
20. 5 M NaOH was used.
21. tBu in toluene; however, significant decomposition was observed. Benzyl alcohol was observed by HPLC suggesting that the CBz group is unstable under these conditions.