Catalytic Asymmetric Insertion of Diazoesters into Aryl-CHO Bonds: Highly Enantioselective Construction of Chiral All-Carbon Quaternary Centers
Lizhu Gao; Byung Chul Kang; Do Hyun Ryu; Journal of the American Chemical Society 135 (2013) 14556–14559; doi:10.1021/ja408196g

data_4120906
_publ_section_title
;
 Catalytic Asymmetric Insertion of Diazoesters into Aryl-CHO Bonds: Highly
 Enantioselective Construction of Chiral All-Carbon Quaternary Centers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14556
_journal_page_last               14559
_journal_paper_doi               10.1021/ja408196g
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H27 Br N2 O2'
_chemical_formula_sum            'C30 H27 Br N2 O2'
_chemical_formula_weight         527.45
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.860(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.785(3)
_cell_length_b                   9.651(3)
_cell_length_c                   14.060(4)
_cell_measurement_reflns_used    1088
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      18.46
_cell_measurement_theta_min      2.33
_cell_volume                     1299.4(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.1003
_diffrn_reflns_av_sigmaI/netI    0.3691
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8031
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    1.611
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.046(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.705
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4920
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      0.704
_refine_ls_R_factor_all          0.1988
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0238P)^2^+1.0704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                1457
_reflns_number_total             4920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja408196g_si_003.cif
_cod_data_source_block           HKSNo1-m
_cod_database_code               4120906