Bis(oxazoline)·copper(I)-catalyzed enantioselective cyclopropanation of cinnamate esters with diazomethane

Tetrahedron Asymmetry

Volumn 14, Issue 7, 2003, Pages 867-872

  Charette, André B ^a   Janes, Marc K ^a   Lebel, Hélène ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; BIS(OXAZOLINE)COPPER; CINNAMIC ACID DERIVATIVE; COPPER COMPLEX; DIAZOMETHANE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CORRELATION ANALYSIS; CYCLOPROPANATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 0037418810     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00076-4     Document Type: Article

References (36)

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23. 2 and MeCN.
24. 2: 332.15, found 333.2; 1g: Burgette, M. I.; Fraile, J. M.; Garcia, J. I.; Garcia-Verdugo, E.; Herrerias, C. I.; Luis, S. V.; Mayoral, J. A. J. Org. Chem. 2001, 66, 8893-8901. 1b, 1c and 1e are commercially available.
25. Since catalysts 1c and 1f exhibited similar reactivity and enantioselectivity, 1c was chosen as the optimal catalyst because it is commercially available.
26. Chiral 1-aminoindan-2-ol derived bis(oxazolines) were also tested and exhibited very low reactivity.
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29. 2, CuCN, CuI and CuBr.
30. 2: C, 80.34; H, 5.39. Found: C, 80.63; H, 5.57%; 2a, 2b, 2c and 2e are commercially available.
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32. 4: C, 57.97; H, 4.38; N, 6.76. Found: C, 57.91; H, 4.33; N, 6.59%.
33. p) since the reaction center is electron rich and directly conjugated with the para-substituent imparting the electronic characteristics of the alkene.
34. 1,5 The diastereoselective [3+2] cycloaddition of diazomethane to alkenes is also known, forming pyrazolines which can be decomposed to cyclopropanes with heat or irradiation. For recent examples, see: (a) Rife, J.; Ortuno, R. M. Tetrahedron: Asymmetry 1999, 10, 4245-4260; (b) Muray, E.; Alvarez-Larena, A.; Piniella, J. F.; Branchadell, V.; Ortuno, R. M. J. Org. Chem. 2000, 65, 388-396. Under our reaction conditions, without catalyst, formation of pyrazolines does not occur and the starting alkene is recuperated quantitatively. Formation of the pyrazoline and subsequent cyclopropane under lewis acidic conditions cannot be excluded as mechanistic possibilities although no enantioselective examples have been reported.
35. 1,5 The diastereoselective [3+2] cycloaddition of diazomethane to alkenes is also known, forming pyrazolines which can be decomposed to cyclopropanes with heat or irradiation. For recent examples, see: (a) Rife, J.; Ortuno, R. M. Tetrahedron: Asymmetry 1999, 10, 4245-4260; (b) Muray, E.; Alvarez-Larena, A.; Piniella, J. F.; Branchadell, V.; Ortuno, R. M. J. Org. Chem. 2000, 65, 388-396. Under our reaction conditions, without catalyst, formation of pyrazolines does not occur and the starting alkene is recuperated quantitatively. Formation of the pyrazoline and subsequent cyclopropane under lewis acidic conditions cannot be excluded as mechanistic possibilities although no enantioselective examples have been reported.
36. 3).