Dynamic Kinetic Resolution of Flavonoids via Asymmetric Allylic Alkylation: Construction of Two Contiguous Stereogenic Centers on Nucleophiles
Liu, Li-Xia; Huang, Wen-Jun; Xie, Qing-Xian; Wu, Bo; Yu, Chang-Bin; Zhou, Yong-Gui; ACS Catalysis  (2021) 12859–12863; doi:10.1021/acscatal.1c03732

data_4519095
_publ_section_title
;
 Dynamic Kinetic Resolution of Flavonoids via Asymmetric Allylic
 Alkylation: Construction of Two Contiguous Stereogenic Centers on
 Nucleophiles
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              12859
_journal_page_last               12863
_journal_paper_doi               10.1021/acscatal.1c03732
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H26 O4'
_chemical_formula_weight         426.49
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.1150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6722(2)
_cell_length_b                   8.2130(2)
_cell_length_c                   12.1784(2)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      139.811
_cell_measurement_theta_min      14.502
_cell_volume                     1149.32(4)
_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 0.982
_diffrn_measured_fraction_theta_max 0.984
_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  0.0649
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19299
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.489
_diffrn_reflns_theta_min         3.687
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.3942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 1662 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(12)
_refine_ls_extinction_coef       0.049(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4042
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0724P)^2^+0.0957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                3812
_reflns_number_total             4042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03732_si_002.cif
_cod_data_source_block           cu_d8v20655_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4519095
_shelx_estimated_absorpt_t_min   0.881
_shelx_estimated_absorpt_t_max   0.950
_shelxl_version_number           2013-4
_shelx_res_checksum              17416
_shelx_hkl_checksum              89576