Palladium-Catalyzed Asymmetric Allylic Alkylation (AAA) with Alkyl Sulfones as Nucleophiles
Trost, Barry M.; Jiao, Zhiwei; Gholami, Hadi; Chemical Science  (2021) –; doi:10.1039/D1SC02599F

data_1563906
_publ_section_title
;
 Palladium-Catalyzed Asymmetric Allylic Alkylation (AAA) with Alkyl
 Sulfones as Nucleophiles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02599F
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N O2 S'
_chemical_formula_sum            'C18 H19 N O2 S'
_chemical_formula_weight         313.40
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2021-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.270(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1212(5)
_cell_length_b                   8.4842(4)
_cell_length_c                   20.1475(10)
_cell_measurement_reflns_used    9222
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.29
_cell_measurement_theta_min      4.39
_cell_volume                     1559.12(14)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32783
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.362
_diffrn_reflns_theta_min         2.193
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    1.894
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       tablet
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2461 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.046(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5761
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0345P)^2^+0.2927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0652
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                5643
_reflns_number_total             5761
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02599f2.cif
_cod_data_source_block           zjd783
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1563906
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.641
_shelx_estimated_absorpt_t_max   0.901
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              99702
_shelx_hkl_checksum              94169