Organocatalytic asymmetric azidation of sulfoxonium ylides: mild synthesis of enantioenriched α-azido ketones bearing a labile tertiary stereocenter.
Guo, Wengang; Jiang, Feng; Li, Shijia; Sun, Jianwei; Chemical science 13 (2022) 11648–11655; doi:10.1039/d2sc03552a

data_1567648
_publ_section_title
;
 Organocatalytic asymmetric azidation of sulfoxonium ylides: mild
 synthesis of enantioenriched \a-azido ketones bearing a labile tertiary
 stereocenter.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              11648
_journal_page_last               11655
_journal_paper_doi               10.1039/d2sc03552a
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H25 N O3'
_chemical_formula_weight         387.46
_chemical_name_systematic
'tert-Butyl (R)-(1-([1,1'-biphenyl]-4-yl)-2-oxo-2-phenylethyl)carbamate'
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-02-02 deposited with the CCDC.	2022-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.1980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5777(2)
_cell_length_b                   41.8595(7)
_cell_length_c                   10.6059(2)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.147
_cell_measurement_theta_min      6.334
_cell_volume                     4249.18(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            39522
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         4.607
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and diethyl ether'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
; 
 Flack x determined using 5988 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1073
_refine_ls_number_reflns         14813
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0626P)^2^+0.1763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                13568
_reflns_number_total             14813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03552a2.cif
_cod_data_source_block           cu_d8v21695_0m
_cod_depositor_comments          'Adding full bibliography for 1567648.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1567648
_shelx_estimated_absorpt_t_min   0.884
_shelx_estimated_absorpt_t_max   0.923
_shelxl_version_number           2013-4
_shelx_res_checksum              75749
_shelx_hkl_checksum              34543