Catalytic enantioselective synthesis of tetrasubstituted chromanones via palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands
Baek, Doohyun; Ryu, Huijeong; Ryu, Ji Yeon; Lee, Junseong; Stoltz, Brian M.; Hong, Sukwon; Chemical Science 11 (2020) 4602–4607; doi:10.1039/D0SC00412J

data_1557750
_publ_section_title
;
 Catalytic enantioselective synthesis of tetrasubstituted chromanones via
 palladium-catalyzed asymmetric conjugate arylation using chiral
 pyridine-dihydroisoquinoline ligands
;
_journal_issue                   18
_journal_name_full               'Chemical Science'
_journal_page_first              4602
_journal_page_last               4607
_journal_paper_doi               10.1039/D0SC00412J
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C20 H22 O2'
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.37
_chemical_name_systematic
(S)-2-(4-(tert-butyl)phenyl)-2-methylchroman-4-one
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-09-20 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9349(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.2747(4)
_cell_length_b                   6.77810(10)
_cell_length_c                   10.2443(2)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.61
_cell_volume                     1615.20(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12536
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.424
_diffrn_reflns_theta_min         1.751
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0306
_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^+0.4895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2880
_reflns_number_total             2965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc00412j2.cif
_cod_data_source_block           hsw58-1
_cod_depositor_comments
;Adding full bibliography for 1557749--1557750.cif.

 Adding full bibliography for 1557749--1557750.cif.
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1557750
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2014-3
_shelx_res_checksum              63886