Palladium-Catalyzed Asymmetric Benzylic Substitution of Secondary Benzyl Carbonates with Nitrogen and Oxygen Nucleophiles.
Najib, Atifah; Hirano, Koji; Miura, Masahiro; Organic letters 19 (2017) 2438–2441; doi:10.1021/acs.orglett.7b01022

data_1546224
_publ_section_title
;
 Palladium-Catalyzed Asymmetric Benzylic Substitution of Secondary Benzyl
 Carbonates with Nitrogen and Oxygen Nucleophiles.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2438
_journal_page_last               2441
_journal_paper_doi               10.1021/acs.orglett.7b01022
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H23 N O2 S'
_chemical_formula_sum            'C25 H23 N O2 S'
_chemical_formula_weight         401.52
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.480(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.717(8)
_cell_length_b                   11.448(8)
_cell_length_c                   10.196(8)
_cell_measurement_reflns_used    3233
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     1048.0(14)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11122
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         3.039
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424.00
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.29
_refine_ls_abs_structure_details
;
 Flack x determined using 1970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.0900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4543
_reflns_number_total             4773
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol7b01022_si_002.cif
_cod_data_source_block           319-2
_cod_database_code               1546224
_shelx_res_checksum              5927
_shelx_hkl_checksum              61029