Asymmetric cyclopropanation catalyzed by C2-symmetric bi(oxazolines)

Tetrahedron Letters

Volumn 41, Issue 7, 2000, Pages 1023-1026

  Boulch, Rachel ^a   Scheurer, Andreas ^a,b   Mosset, Paul ^a   Saalfrank, Rolf W ^b  

^a Lab Chim Synt/Activations Biomol   (France)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Alkenes; Asymmetric reactions; Copper; Copper compounds; Cyclopropanation

Indexed keywords

ALKENE; COPPER DERIVATIVE; CYCLOPROPANE; MAGNESIUM SULFATE; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; LIGAND BINDING; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY;

EID: 0034639721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02220-0     Document Type: Article

References (18)

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7. (f) For reviews, see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339-345, Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919-7946 and Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
8. (f) For reviews, see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339-345, Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919-7946 and Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
9. (f) For reviews, see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339-345, Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919-7946 and Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
10. The first uses of this new type of ligands were achieved for hydrosilylation: Lee, S.-g.; Lim, C. W.; Song, C. E.; Kim, I. O.; Jun, C.-H. Tetrahedron: Asymmetry 1997, 8, 2927-2932.
11. Ebinger, A.; Heinz, T.; Umbricht, G.; Pfaltz, A. Tetrahedron 1998, 54, 10469-10480.
12. 2: C, 76.41; H, 8.90; N, 6.86. Found: C, 76.31; H, 8.96; N, 6.82.
13. Scheurer, A.; Mosset, P.; Saalfrank, R. W. Tetrahedron: Asymmetry 1997, 8, 1243-1251 and 3161.
14. Congreve, M. S.; Davison, E. C.; Fuhry, M. A. M.; Holmes, A. B.; Payne, A. N.; Robinson, R. A.; Ward, S. E. Synlett 1993, 663-664.
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16. No surface effect was observed. For an example of a surface effect with molecular sieves, see: Gothelf, K. V.; Hazell, R. G.; Jørgensen K. A. J. Org. Chem. 1998, 63, 5483-5488.
17. 2 (1 mL) was added during 5 h at 0°C and stirring was continued for 16 h at ca. 20°C.
18. Very recently, the first example of a catalyst which gives predominantly the cis-isomer was reported: Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1163-1165.