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Volumn 131, Issue 40, 2009, Pages 14584-14589

Heterogeneously catalyzed asymmetric hydrogenation of C=C bonds directed by surface-tethered chiral modifiers

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUPS; ASYMMETRIC HYDROGENATION; ASYMMETRIC INDUCTION; BULKY SUBSTITUENTS; C-C BONDS; CARBON SUPPORT; CATALYTIC HYDROGENATION; CHIRAL MODIFIERS; CHIRAL SULFIDE; ENAMINES; ENANTIO-DIFFERENTIATING; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; ENANTIOSELECTIVE REACTIONS; HIGH RESOLUTION; HOMOGENEOUS CATALYST; IMINIUM; ISLAND FORMATION; ISOPHORONES; LIGAND ADSORPTION; LIGAND MOLECULES; METAL SURFACES; ORGANIC SYNTHESIS; PD NANO PARTICLE; PRODUCT MOLECULES; PYRROLIDINES; RACEMIC PRODUCTS; SMALL SUBSTITUENTS; TERTIARY AMINE; TURNOVER NUMBER; XPS DATA;

EID: 70349918467     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906356g     Document Type: Article
Times cited : (42)

References (29)
  • 15
    • 38349178582 scopus 로고    scopus 로고
    • For recent reviews of organocatalysis with catalysts bearing a pyrrolidine motif see: (a)
    • For recent reviews of organocatalysis with catalysts bearing a pyrrolidine motif see: (a) Erkkila, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416-5470.
    • (2007) Chem. Rev. , vol.107 , pp. 5416-5470
    • Erkkila, A.1    Majander, I.2    Pihko, P.M.3
  • 23
    • 70349937603 scopus 로고    scopus 로고
    • note
    • In our case the ligand does not cause rate enhancement, unlike the case of Pt-catalyzed ketoester hydrogenation, which involves a different mechanism. Such effects are specific to the reaction in question.
  • 25
    • 70349957709 scopus 로고    scopus 로고
    • note
    • We define enantioselective turn-over number as (product ee x product yield)/(ligand loading x ligand ee); if this number is >1 then enantioselective catalysis has occurred.
  • 26
    • 70349946801 scopus 로고    scopus 로고
    • note
    • Another mechanistic possibility involves the delivery of the isophorone to the metal surface via hydrogen bonding with the secondary amine of the ligand. This would also account for the production of racemic TMCH with the tertiary amine ligand 7, although it is less likely given the previous observation of the condensation product with proline and the lack of asymmetric induction in this reaction by other chiral modifiers with a capacity to hydrogen bond.
  • 27
    • 70349956184 scopus 로고    scopus 로고
    • note
    • The ligands 8 were prepared from (S)-β-homoproline in an analogous manner to the preparation of the ligands 1-6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.