Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron Transfer: Development of an Asymmetric Aza-Pinacol Cyclization
Lydia J. Rono; Hatice G. Yayla; David Y. Wang; Michael F. Armstrong; Robert R. Knowles; Journal of the American Chemical Society 135 (2013) 17735–17738; doi:10.1021/ja4100595

data_4121242
_publ_section_title
;
 Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron
 Transfer: Development of an Asymmetric Aza-Pinacol Cyclization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17735
_journal_page_last               17738
_journal_paper_doi               10.1021/ja4100595
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H22 Br Cl N2 O'
_chemical_formula_weight         349.70
_chemical_name_common            C14H22BrClN2O
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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           'APEX2 v2013.4-1'
_cell_angle_alpha                90
_cell_angle_beta                 94.47(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7790(8)
_cell_length_b                   10.6400(13)
_cell_length_c                   12.4930(15)
_cell_measurement_reflns_used    121
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.2114
_cell_measurement_theta_min      4.1813
_cell_volume                     765.84(17)
_computing_cell_refinement       'APEX2 v2013.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5144
_diffrn_reflns_theta_full        66.02
_diffrn_reflns_theta_max         66.02
_diffrn_reflns_theta_min         3.55
_diffrn_source                   'ImuS micro-focus source'
_exptl_absorpt_coefficient_mu    5.213
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'translucent pale yellow'
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.358
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.033(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2301
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.0101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0665
_reflns_number_gt                2285
_reflns_number_total             2301
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4100595_si_002.cif
_cod_data_source_block           report_cif
_cod_original_cell_volume        765.8(16)
_cod_database_code               4121242