Asymmetric Synthesis of P-Stereogenic Compounds via Thulium(III)-Catalyzed Desymmetrization of Dialkynylphosphine Oxides
Zhang, Yu; Zhang, Fengcai; Chen, Long; Xu, Jian; Liu, Xiaohua; Feng, Xiaoming; ACS Catalysis 9 (2019) 4834–; doi:10.1021/acscatal.9b00860

data_4514776
_publ_section_title
;
 Asymmetric Synthesis of P-Stereogenic Compounds via
 Thulium(III)-Catalyzed Desymmetrization of Dialkynylphosphine Oxides
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              4834
_journal_paper_doi               10.1021/acscatal.9b00860
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H25 O3 P S'
_chemical_formula_weight         460.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6131(4)
_cell_length_b                   35.7850(11)
_cell_length_c                   9.9738(3)
_cell_measurement_reflns_used    9746
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      71.82
_cell_measurement_theta_min      2.47
_cell_volume                     4858.7(3)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            49356
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.376
_diffrn_reflns_theta_min         3.474
_exptl_absorpt_coefficient_mu    2.010
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       BAR
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 3065 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         9250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0488P)^2^+0.8006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                7954
_reflns_number_total             9250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b00860_si_002.cif
_cod_data_source_block           cu_20180607_ZY_04_0ma_a
_cod_database_code               4514776
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.623
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              69973
_shelx_hkl_checksum              50807