Catalytic asymmetric hydrogenation of heteroaromatic compounds, indoles [12]

Journal of the American Chemical Society

Volumn 122, Issue 31, 2000, Pages 7614-7615

  Kuwano, Ryoichi ^a   Sato, Koji ^a   Kurokawa, Takashi ^a   Karube, Daisuke ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HYDROGENATION; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034625892     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001271c     Document Type: Letter

References (32)

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21. Representative results of using commercially available chiral bisphosphines were as follows: (R)-BINAP, 1% ee (S); (R)-(S)-BPPFA, 0% ee; (2S,3S)-Chiraphos, 1% ee (S); (-)-(2R, 3R)-DIOP, 0% ee; (2S, 4S)-BPPM, 0% ee; (R,R)-Me-DuPHOS, 0% ee.
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30. 1H NMR analysis). However, the exchange of hydrogen for deuterium on the N-acetyl group was observed in this case.
31. The reactions in other solvents also proceeded with high enantioselectivity and good catalyst activity: 92% conversion, 91% ee in toluene; 53% conversion, 87% ee in 1,2-dichloroethane; 52% conversion, 84% ee in THF.
32. 3N catalyst, 10O °C, 10.0 MPa, 0.5 h).