Design of new chiral phase-transfer catalysts with dual functions for highly enantioselective epoxidation of α,β-unsaturated ketones

Journal of the American Chemical Society

Volumn 126, Issue 22, 2004, Pages 6844-6845

  Ooi, Takashi ^a   Ohara, Daisuke ^a   Tamura, Masazumi ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BINAPHTHYL; CHALCONE; CINCHONA ALKALOID; HYPOCHLORITE SODIUM; KETONE DERIVATIVE; QUATERNARY AMMONIUM BROMIDE; QUATERNARY AMMONIUM DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CHIRALITY; CRYSTALLIZATION; ENANTIOSELECTIVITY; EPOXIDATION; HYDROGEN BOND; METHODOLOGY; PHASE TRANSITION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 3042815030     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048600b     Document Type: Article

References (23)

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21. Ooi, T.; Uematsu, Y.; Kameda, M.; Maruoka, K. Angew. Chem., Int. Ed. 2002, 41, 1551. Control experiments revealed that a structurally rigid heterochiral catalyst exhibited higher chiral efficiency than a homochiral one in the present epoxidation. See the Supporting Information.
22. The catalyst 1e can be recovered quantitatively by chromatographic separation and reused for this epoxidation at least five times without decrease of catalytic activity and enantioselectivity.
23. For detailed crystallographic data, see the Supporting Information.