Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.
Li, Beryl X.; Le, Diane N.; Mack, Kyle A.; McClory, Andrew; Lim, Ngiap-Kie; Cravillion, Theresa; Savage, Scott; Han, Chong; Collum, David B.; Zhang, Haiming; Gosselin, Francis; Journal of the American Chemical Society 139 (2017) 10777–10783; doi:10.1021/jacs.7b05071

data_4131359
_publ_section_title
;
 Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon
 Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10777
_journal_page_last               10783
_journal_paper_doi               10.1021/jacs.7b05071
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H24 O4 S'
_chemical_formula_weight         408.49
_chemical_name_common            71462-057
_chemical_name_systematic        gene767
_space_group.centring_type       primitive
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.418(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8872(7)
_cell_length_b                   6.0338(5)
_cell_length_c                   21.8424(19)
_cell_measurement_reflns_used    5496
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.58
_cell_volume                     1039.16(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15929
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         1.865
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
; 
 Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.11(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0501P)^2^+0.2347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                3108
_reflns_number_total             3617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja-2017-050714-File015.cif
_cod_data_source_block           71462-057
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4131359
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              1839
_shelx_hkl_checksum              86187