Enantioselective β-Boration of Acyclic Enones by a [2.2]Paracyclophane-Based N-Heterocyclic Carbene Copper(I) Catalyst
Lei Zhao; Yudao Ma; Fuyan He; Wenzeng Duan; Jianqiang Chen; Chun Song; Journal of Organic Chemistry 78 (2013) 1677–1681; doi:10.1021/jo302694d

data_4027967
_publ_section_title
;
 Enantioselective \b-Boration of Acyclic Enones by a
 [2.2]Paracyclophane-Based N-Heterocyclic Carbene Copper(I) Catalyst
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1677
_journal_page_last               1681
_journal_paper_doi               10.1021/jo302694d
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C27 H30 Cl N3 O3'
_chemical_formula_weight         479.99
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.174(4)
_cell_length_b                   11.595(4)
_cell_length_c                   23.778(10)
_cell_measurement_temperature    273(2)
_cell_volume                     2529.3(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12585
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9729
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.117
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0905P)^2^+0.6606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1698
_reflns_number_gt                2922
_reflns_number_total             4475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302694d_si_001.cif
_cod_data_source_block           test
_cod_original_cell_volume        2529.2(17)
_cod_database_code               4027967