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Volumn 21, Issue 13-14, 2010, Pages 1722-1729

Insight into the structure of the precatalyst and active species for samarium iodo binaphtholate catalysed aminolysis of epoxides

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 METHOXYPHENYLAMINO) CYCLOHEXANOL; 2 (4 METHOXYPHENYLAMINO) CYCLOHEXANOL; 4 OXA 2 (2 METHOXYPHENYLAMINO)CYCLOPENTANOL; 4 OXA 2 (4 METHOXYPHENYLAMINO)CYCLOPENTANOL; EPOXIDE; SAMARIUM; SAMARIUM IODO BINAPHTHOLATE; TERT BUTYL 3 HYDROXY 4 (2 METHOXYPHENYLAMINO) PYRROLIDINE 1 CARBOXYLATE; TERT BUTYL 3 HYDROXY 4 (2 METHOXYPHENYLAMINO)PYRROLIDINE 1 CARBOXYLATE; TERT BUTYL 3 HYDROXY 4 (4 METHOXYPHENYLAMINO)PYRROLIDINE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

EID: 77956266607     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.04.035     Document Type: Article
Times cited : (8)

References (77)
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    • Shibasaki, M.1    Sasai, H.2
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    • Schneider, C.1
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    • For a review on non-linear effects in lanthanide catalysed reactions see: J. Inanaga, H. Futuno, and T. Hayano Chem. Rev. 102 2002 2211 2225
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    • Inanaga, J.1    Futuno, H.2    Hayano, T.3
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    • note
    • If monomeric and dimeric catalytic species promoting the reaction with different asymmetric inductions are in equilibrium the ratio of these species and thus the enantiomeric excess of the product should vary with the concentration of reaction mixture. However when the ring opening of 2,5-dihydrofuran oxide 2d with p-anisidine 3b was performed at various concentrations the variation of the enantiomeric excess of aminoalcohol 4db was too small for supporting our proposal.
  • 70
    • 77956263911 scopus 로고    scopus 로고
    • note
    • To probe the possibility of the involvement of enantioenriched β-aminoalcohol in the active species the enantiomeric excess of product was monitored during the aminolysis of 2d with p-anisidine. No significant variation was observed when measuring enantiomeric excesses of 4db on aliquots of reaction mixture and it was not possible to conclude on the possible role of β-aminoalcohol as a samarium ligand in these reactions.


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