First iminodiazaphospholidines with a stereogenic phosphorus center. Application to asymmetric copper-catalyzed cyclopropanation

Journal of the American Chemical Society

Volumn 121, Issue 24, 1999, Pages 5807-5808

  Brunel, Jean Michel ^a   Legrand, Olivier ^a   Reymond, Sébastien ^a   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; CYCLOPROPANE DERIVATIVE; PHOSPHORANE DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0033597638     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984295g     Document Type: Article

References (45)

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34. 18
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44. Copper(II) triflate complexes do not catalyze the reaction unless they are heated to 65 °C. Other Cu(I) and Cu(II) salts (for example, halide, cyanide, acetate, and perchlorate) show little or no catalytic activity, and the observed enantioselectivity is markedly inferior to that obtained for the triflate-ligand complexes.
45. It is interesting to note that compounds 3, 6a, and 6b do not function as imido donor groups for the aziridination of styrene catalyzed by CuOTf. On the other hand, the corresponding ligands 2, 5a, 5b do not lead to the formation with high level of enantioselectivity to the cyclopropane adducts 10 and 11 (enantioselectivity up to 7% ee).