Chiral Bifunctional Phosphine Ligand Enabling Gold-Catalyzed Asymmetric Isomerization of Alkyne to Allene and Asymmetric Synthesis of 2,5-Dihydrofuran.
Cheng, Xinpeng; Wang, Zhixun; Quintanilla, Carlos D.; Zhang, Liming; Journal of the American Chemical Society 141 (2019) 3787–3791; doi:10.1021/jacs.8b12833

data_4128523
_publ_section_title
;
 Chiral Bifunctional Phosphine Ligand Enabling Gold-Catalyzed Asymmetric
 Isomerization of Alkyne to Allene and Asymmetric Synthesis of
 2,5-Dihydrofuran.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3787
_journal_page_last               3791
_journal_paper_doi               10.1021/jacs.8b12833
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C43 H55 Au Cl F3 N P'
_chemical_formula_weight         906.26
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.99(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.810(9)
_cell_length_b                   10.578(6)
_cell_length_c                   14.298(10)
_cell_measurement_reflns_used    1462
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      18.8
_cell_measurement_theta_min      2.33
_cell_volume                     1908(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.1565
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13887
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.623
_diffrn_reflns_theta_min         1.446
_exptl_absorpt_coefficient_mu    4.013
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       needle
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         2.490
_refine_diff_density_min         -3.244
_refine_diff_density_rms         0.237
_refine_ls_abs_structure_details
;
 Flack x determined using 1703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(11)
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         7570
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0667
_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^)+(0.0435P)^2^+10.3177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                5304
_reflns_number_total             7570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12833_si_002.cif
_cod_data_source_block           z08132018_3_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4128523
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.501
_shelx_estimated_absorpt_t_max   0.825
_shelx_res_checksum              18620
_shelx_hkl_checksum              31382