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Volumn , Issue 2, 2001, Pages 275-291

(β-amino alcohol)(arene)ruthenium(II)-catalyzed asymmetric transfer hydrogenation of functionalized ketones - Scope, isolation of the catalytic intermediates, and deactivation processes

Author keywords

Amino alcohols; Asymmetric catalysis; Hydrogen transfer; Intermediates; Ruthenium

Indexed keywords

4 TOLYLSULFONYL 1,2 DIPHENYLETHYLENEDIAMINE; ALCOHOL DERIVATIVE; KETONE; POLYCYCLIC AROMATIC HYDROCARBON; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0035133308     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200101)2001:2<275::aid-ejoc275>3.3.co;2-e     Document Type: Article
Times cited : (94)

References (58)
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    • note
    • [8b]).
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    • note
    • Poor results were also obtained using (1R,2R)-diphenylethylenediamine or the corresponding N-acetyl derivative.
  • 27
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    • note
    • 2/9b at room temperature, respectively.
  • 28
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    • WO Pat. Appl. 98 42643 (26.03.1997) to Zeneca Ltd. For recent developments concerning rhodium and iridium complexes with diamine ligands in asymmetric transfer hydrogenation of ketones using 2-propanol as the hydrogen donor, see
    • [17a] WO Pat. Appl. 98 42643 (26.03.1997) to Zeneca Ltd. For recent developments concerning rhodium and iridium complexes with diamine ligands in asymmetric transfer hydrogenation of ketones using 2-propanol as the hydrogen donor, see:
  • 39
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    • [22a] For the synthesis of optically active phthalides through ruthenium-catalyzed asymmetric hydrogenation of o-acylbenzoic esters, see: T. Okhuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5509-5512
    • Okhuma, T.1    Kitamura, M.2    Noyori, R.3
  • 44
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    • note
    • 6 are similar to those of 35 (see Exp. Sect.), and are consistent with the highly stereoselective formation of a major diastereomer. Attempted preparations of the active species derived from ephedrine, i.e. 36b and 37b, have so far yielded only mixtures of products.
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    • note
    • [21]
  • 55
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    • note
    • As remarked pertinently by a referee, the deactivation process of catalytic species by functionalized ketones discussed in this section do not account for the gradual deactivation of the catalytic systems based on (2-hydroxymethyl)pyrrolidine (14), which takes place even with acetophenone. In this case, it is possible that deactivation is due to a low, inherent stability of in situ formed Ru species.
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    • [32a] For a review on developments in combinatorial and rapid screening in homogeneous catalysis, see: R. H. Crabtree, Chem. Commun. 1999, 1611-1616.
    • (1999) Chem. Commun. , pp. 1611-1616
    • Crabtree, R.H.1
  • 57
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    • [32b] For an application to the asymmetric reduction of ketones, see: H. B. Kagan, J. Organomet. Chem. 1998, 567, 3.
    • (1998) J. Organomet. Chem. , vol.567 , pp. 3
    • Kagan, H.B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.