A new catalytic and enantioselective desymmetrization of symmetrical methylidene cycloalkene oxides

Organic Letters

Volumn 2, Issue 7, 2000, Pages 933-936

  Bertozzi, Fabio ^a   Crotti, Paolo ^a   Macchia, Franco ^a   Pineschi, Mauro ^a   Arnold, Alexander ^b   Feringa, Ben L ^b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001423271     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005584o     Document Type: Article

References (24)

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18. The corresponding blank reactions performed without the chiral ligands gave a complex reaction mixture containing adducts 4 and 5 in a 1:1 ratio. For a review of ligand-accelerated catalysis, see: Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.
19. 3)]. Enantioselectivity determined by chiral GC (CP-cyclodex-β-column). Following the above typical procedure employing vinyloxirane 8 (Table 2, entry 2), the reaction was performed on a 2 mmol scale (see the Supporting Information).
20. The terms matched and mismatched ligands refer to the addition of diethylzinc to 2-cyclohexenone. When these chiral ligands (2.4 mol %) were used as catalysts for this reaction, (S,S,S)-1 afforded 3-ethylcyclohexanone with an 82% yield and 75% ee, while (S,R,R)-2 gave the same product in 95% yield and >98% ee (see ref 8b).
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