Enantioselective synthesis of planar chiral azaferrocenes via chiral ligand-mediated ring- and lateral-lithiations

Tetrahedron Letters

Volumn 44, Issue 40, 2003, Pages 7503-7506

  Fukuda, Tsutomu ^a   Imazato, Kengo ^a   Iwao, Masatomo ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1',2',3',4',5' PENTAMETHYLAZAFERROCENE; 1',2,2',3',4',5,5' HEPTAMETHYLAZAFERROCENE; ETHER; FERROCENE DERIVATIVE; LIGAND; OXAZOLINE DERIVATIVE; SPARTEINE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; LITHIATION; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0041333887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.010     Document Type: Article

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20. 2, ethyl acetate) to give 2-hydroxymethyl-1′,2′,3′,4′,5′ -pentamethylazaferrocene ( 2a ) (70.0 mg, 70%). Enantiomeric excess of the product 2a was determined to be 81% ee by HPLC analysis (Daicel Chiralpak AD, hexane-i-PrOH=9:1).
21. 2, hexane-ethyl acetate=5:1 to 3:1) to give 2-(2,2-diphenyl-2-hydroxyethyl)-1′,2′,3′,4′,5, 5′-hexamethylazaferrocene ( 7a ) (93.0 mg, 57%). Enantiomeric excess of the product 7a was determined to be 99% ee by HPLC analysis (Daicel Chiralpak AD, hexane-i-PrOH=19:1).