Enantioselective Metal/Organo-Catalyzed Aerobic Oxidative sp3 C-H Olefination of Tertiary Amines Using Molecular Oxygen as the Sole Oxidant
Gen Zhang; Yunxia Ma; Shoulei Wang; Yaohu Zhang; Rui Wang; Journal of the American Chemical Society 134 (2012) 12334–12337; doi:10.1021/ja303333k

data_4118393
_publ_section_title
;
 Enantioselective Metal/Organo-Catalyzed Aerobic Oxidative sp3 C-H
 Olefination of Tertiary Amines Using Molecular Oxygen as the Sole Oxidant
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12334
_journal_page_last               12337
_journal_paper_doi               10.1021/ja303333k
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C19 H18 Cl N O2'
_chemical_formula_weight         327.79
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.67(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.634(19)
_cell_length_b                   7.46(2)
_cell_length_c                   16.24(4)
_cell_measurement_reflns_used    788
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.24
_cell_measurement_theta_min      2.51
_cell_volume                     803(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0794
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3105
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9615
_exptl_absorpt_correction_T_min  0.9385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0671P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                1500
_reflns_number_total             2363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303333k_si_002.cif
_cod_data_source_block           p21
_cod_database_code               4118393