Direct Asymmetric Michael Reactions of Cyclic 1,3-Dicarbonyl Compounds and Enamines Catalyzed by Chiral Bisoxazoline-Copper(II) Complexes
Nis Halland; Thomas Velgaard; Karl Anker Jørgensen; Journal of Organic Chemistry 68 (2003) 5067–5074; doi:10.1021/jo0343026

data_4022439
_publ_contact_author
; Karl Anker Jorgensen
  Institute of Chemistry
  Aarhus Univerity
  DK 8000, Aarhus C
;
_publ_section_title
;
 Direct Asymmetric Michael Reactions of Cyclic 1,3-Dicarbonyl
 Compounds and Enamines Catalyzed by Chiral
 Bisoxazoline-Copper(II) Complexes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5067
_journal_page_last               5074
_journal_paper_doi               10.1021/jo0343026
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C20 H15 Cl O6'
_chemical_formula_sum            'C20 H15 Cl O6'
_chemical_formula_weight         386.80
_chemical_name_systematic
;                                   
4-(4-Chloro-phenyl)-4-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxo-butyric acid 
methyl ester
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   5.284(1)
_cell_length_b                   14.857(3)
_cell_length_c                   21.982(4)
_cell_measurement_reflns_used    3955
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.3
_cell_volume                     1725.7(6)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;                                   
      ORTEP-III (Burnett & Johnson,  1996), KRYSTAL                     
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;                                   
     SIR97 (Altomare et al., 1997 ), KRYSTAL                            
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 99.8
_diffrn_measured_fraction_theta_max 99.2
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       '\w rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.153
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21710
_diffrn_reflns_reduction_process 21710
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   XPREP,1995
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          .56
_exptl_crystal_size_mid          .09
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.6(1)
_refine_diff_density_min         -0.5(1)
_refine_ls_abs_structure_details
; Least squares refinement based on all 2856 significant reflections 
including 1043 Bijvoet pairs included a parameter according to Rogers,
1981, establishing the chirality beyond any doubt.  
;
_refine_ls_abs_structure_Rogers  0.87(18)
_refine_ls_extinction_coef       138(18)
_refine_ls_extinction_method
'  Type 1 Lorentzian isotropic (Becker and Coppens, 1974)           '
_refine_ls_goodness_of_fit_ref   1.14
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.00002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;                                   
w= 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^- |F|}^2^                           
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.047
_reflns_number_gt                2856
_reflns_number_total             5297
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            jo0343026si20030307_071433.cif
_cod_data_source_block           nh_3b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 27 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4022439