Highly Asymmetric Intramolecular Cyclopropanation of Acceptor-Substituted Diazoacetates by Co(II)-Based Metalloradical Catalysis: Iterative Approach for Development of New-Generation Catalysts
Xue Xu; Hongjian Lu; Joshua V. Ruppel; Xin Cui; Silke Lopez de Mesa; Lukasz Wojtas; X. Peter Zhang; Journal of the American Chemical Society 133 (2011) 15292–15295; doi:10.1021/ja2062506

data_4106880
_publ_section_title
;
 Highly Asymmetric Intramolecular Cyclopropanation of Acceptor-Substituted
 Diazoacetates by Co(II)-Based Metalloradical Catalysis: Iterative
 Approach for Development of New-Generation Catalysts
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15292
_journal_page_last               15295
_journal_paper_doi               10.1021/ja2062506
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 O5'
_chemical_formula_sum            'C21 H20 O5'
_chemical_formula_weight         352.37
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7269(3)
_cell_length_b                   8.3487(5)
_cell_length_c                   35.6555(17)
_cell_measurement_reflns_used    1930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      52.3
_cell_measurement_theta_min      2.45
_cell_volume                     1704.77(16)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            14389
_diffrn_reflns_theta_full        66.20
_diffrn_reflns_theta_max         66.20
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.9686
_exptl_absorpt_correction_T_min  0.8891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.2850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                2560
_reflns_number_total             2890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2062506_si_006.cif
_cod_data_source_block           4
_cod_database_code               4106880