Nucleophile-Dependent Z/ E- and Regioselectivity in the Palladium-Catalyzed Asymmetric Allylic C-H Alkylation of 1,4-Dienes.
Lin, Hua-Chen; Xie, Pei-Pei; Dai, Zhen-Yao; Zhang, Shuo-Qing; Wang, Pu-Sheng; Chen, Yu-Gen; Wang, Tian-Ci; Hong, Xin; Gong, Liu-Zhu; Journal of the American Chemical Society 141 (2019) 5824–5834; doi:10.1021/jacs.8b13582

data_4128394
_publ_section_title
;
 Nucleophile-Dependent Z/ E- and Regioselectivity in the
 Palladium-Catalyzed Asymmetric Allylic C-H Alkylation of 1,4-Dienes.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5824
_journal_page_last               5834
_journal_paper_doi               10.1021/jacs.8b13582
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H24 Cl N O4'
_chemical_formula_weight         413.88
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.51750(10)
_cell_length_b                   10.26040(10)
_cell_length_c                   22.8870(3)
_cell_measurement_reflns_used    5794
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.0310
_cell_measurement_theta_min      3.8380
_cell_volume                     2234.99(4)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7854
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.194
_diffrn_reflns_theta_min         3.863
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1654 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.007(6)
_refine_ls_extinction_coef       0.0066(5)
_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   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0510P)^2^+0.2059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                4064
_reflns_number_total             4211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13582_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4128394
_shelx_estimated_absorpt_t_min   0.615
_shelx_estimated_absorpt_t_max   0.701
_shelxl_version_number           2013-4
_shelx_res_checksum              85095
_shelx_hkl_checksum              30964