Cobalt-Catalyzed Asymmetric Cyclopropanation with Diazosulfones: Rigidification and Polarization of Ligand Chiral Environment via Hydrogen Bonding and Cyclization
Shifa Zhu; Joshua V. Ruppel; Hongjian Lu; Lukasz Wojtas; X. Peter Zhang; Journal of the American Chemical Society 130 (2008) 5042–5043; doi:10.1021/ja7106838

data_4107681
_publ_section_title
;
 Cobalt-Catalyzed Asymmetric Cyclopropanation with Diazosulfones:
 Rigidification and Polarization of Ligand Chiral Environment via Hydrogen
 Bonding and Cyclization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5042
_journal_page_last               5043
_journal_paper_doi               10.1021/ja7106838
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_sum            'C68 H66 N8 O12'
_chemical_formula_weight         1187.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 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                   10.3608(19)
_cell_length_b                   25.392(5)
_cell_length_c                   22.380(4)
_cell_measurement_temperature    100(2)
_cell_volume                     5887.8(19)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'BRUKER SMART 1K CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34062
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.9463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       polyhedra
_exptl_crystal_F_000             2504
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0504P)^2^+2.0594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                3513
_reflns_number_total             3948
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7106838-file004.cif
_cod_data_source_block           ZhuPhyrinP6
_cod_database_code               4107681