메뉴 건너뛰기




Volumn 6, Issue 6, 1995, Pages 1441-1450

Dramatic solvents effects on the enantioselectivity of chiral oxazaborolidine catalyzed asymmetric 1,3-dipolar cycloadditions of nitrones with ketene acetals

Author keywords

[No Author keywords available]

Indexed keywords

1,3,2 OXAZABOROLIDINE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; ORGANOBORON DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029033931     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00177-Q     Document Type: Article
Times cited : (93)

References (85)
  • 12
    • 0002562810 scopus 로고
    • Asymmetric 1,3-Dipolar Cycloaddition of Cyclic Nitrones to Crotonic Acid Derivatives Bearing Chiral Auxiliaries. Synthesis of Optically Active β-Amino Acids, (+)-Sedridine, and (+)-Hygroline
    • (ref. 2 and 3 cited therein)
    • (1993) Synlett , pp. 395-396
    • Murahashi1    Imada2    Kohno3    Kawakami4
  • 20
    • 0002689641 scopus 로고
    • Tandem Transesterification and Diastereoselective Intramolecular Cycloaddition of α-Methoxycarbonylnitrones with Chiral Acyclic Allyl Alcohols
    • (1994) Synlett , pp. 620-622
    • Tamura1    Yamaguchi2    Okabe3    Sakamoto4
  • 34
    • 84914087360 scopus 로고    scopus 로고
    • The alternative concerted reaction mechanism via an endo-approach of the ketene acetal would be accompanied by unfavoured steric interactions between the 2-methyl substituent of the ketene acetal and the C-phenyl group of the nitrone.
  • 44
    • 85045552781 scopus 로고
    • A Convenient Method for the Preparation of Enantiomerically Pure 2-SubstitutedN-Tosylaziridines
    • (1992) Synlett , pp. 41-44
    • Berry1    Craig2
  • 46
    • 0000621846 scopus 로고
    • Empirische Parameter der Lösungsmittelpolarität als lineare „Freie Enthalpie”-Beziehungen
    • (1979) Angewandte Chemie , vol.91 , pp. 119-131
    • Reichardt1
  • 48
    • 84914087359 scopus 로고    scopus 로고
    • Only 2% ee was obtained when the 3a-catalyzed reaction was performed in THF as solvent.
  • 49
    • 0027160174 scopus 로고
    • For examples of solvent-dependent enantioselectivity in chiral Lewis acid catalyzed asymmetric Diels-Alder and aldol reactions, see:
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3979-3982
    • Corey1    Loh2
  • 54
    • 0001859019 scopus 로고
    • Transition Metal-catalyzed Asymmetric Vinylcyclopropane-Cyclopentene Rearrangements with Chiral Phosphine Ligands. Dramatic Solvent Effects on Asymmetric Induction.
    • In other reactions:
    • (1992) Chemistry Letters , pp. 2329
    • Hiroi1    Arinaga2    Ogino3
  • 63
    • 84914087357 scopus 로고    scopus 로고
    • the role of nitroethane is more difficult to understand. Strong solvation of the nitrone may hinder the usual attack of the ketene acetal. Attack on the rear side may be faster than desolvation.
  • 67
    • 0028130028 scopus 로고
    • Reviews on stereoselective preparation of β-amino acids:
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole1
  • 73
    • 84914087356 scopus 로고    scopus 로고
    • The use of o-xylene, m-xylene or naphtalene as co-solvents did not improve the enantioselectivity.
  • 74
    • 84914087355 scopus 로고    scopus 로고
    • 3-complexes we found that E- and Z-nitrones can isomerize rapidly in the presence of Lewis acids
  • 85
    • 84914087352 scopus 로고    scopus 로고
    • Financial support by the Innovation Oriented Research Program (IOP) on Catalysis (no. 90034) of the Netherlands Ministry of Economic Affairs is gratefully acknowledged.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.