Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.
Zhu, Rong; Buchwald, Stephen L.; Journal of the American Chemical Society 137 (2015) 8069–8077; doi:10.1021/jacs.5b04821

data_4123865
_publ_section_title
;
 Versatile Enantioselective Synthesis of Functionalized Lactones via
 Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8069
_journal_page_last               8077
_journal_paper_doi               10.1021/jacs.5b04821
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H15 Br2 N3 O2'
_chemical_formula_weight         477.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1816(11)
_cell_length_b                   11.0851(15)
_cell_length_c                   21.848(3)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      3.38
_cell_volume                     1739.3(4)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            37176
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         1.864
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    4.681
_exptl_absorpt_correction_T_max  0.5645
_exptl_absorpt_correction_T_min  0.4825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
; 
 Flack x determined using 1684 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.004(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4912
_refine_ls_number_restraints     387
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0283P)^2^+1.7825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4277
_reflns_number_total             4912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b04821_si_002.cif
_cod_data_source_block           X14147
_cod_depositor_comments          'Adding full bibliography for 4123865.cif.'
_cod_database_code               4123865
_shelx_estimated_absorpt_t_min   0.627
_shelx_estimated_absorpt_t_max   0.933
_shelxl_version_number           2014-2
_shelx_res_checksum              14960
_shelx_hkl_checksum              74569