Diastereoselective carbonyl allylation with simple olefins enabled by palladium complex-catalyzed C-h oxidative borylation.
Tao, Zhong-Lin; Li, Xing-Han; Han, Zhi-Yong; Gong, Liu-Zhu; Journal of the American Chemical Society 137 (2015) 4054–4057; doi:10.1021/jacs.5b00507

data_4123548
_publ_section_title
;
 Diastereoselective carbonyl allylation with simple olefins enabled by
 palladium complex-catalyzed C-h oxidative borylation.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4054
_journal_page_last               4057
_journal_paper_doi               10.1021/jacs.5b00507
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C24 H21 N O2'
_chemical_formula_weight         355.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                97.165(5)
_cell_angle_beta                 104.869(4)
_cell_angle_gamma                94.914(4)
_cell_formula_units_Z            2
_cell_length_a                   9.069(2)
_cell_length_b                   9.142(2)
_cell_length_c                   11.705(3)
_cell_measurement_reflns_used    1241
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      52.651
_cell_measurement_theta_min      4.683
_cell_volume                     923.6(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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6743
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.821
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0523P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2512
_reflns_number_total             3626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b00507_si_002.cif
_cod_data_source_block           DM14787
_cod_database_code               4123548
_shelxl_version_number           2014-3
_shelx_res_checksum              44429
_shelx_hkl_checksum              83930