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_1557749
_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_absolute_configuration ad
_chemical_formula_moiety         'C26 H25 Cl2 F3 N2 Pd, C1 H2 Cl2'
_chemical_formula_sum            'C27 H27 Cl4 F3 N2 Pd'
_chemical_formula_weight         684.71
_chemical_name_systematic
'((S)-3-(2,6-diethylbenzyl)-1-(5-(trifluoromethyl)pyridin-2-yl)-3,4-dihydroisoquinoline) palladium(II) chloride'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Heat-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3222(2)
_cell_length_b                   16.3645(5)
_cell_length_c                   22.9119(6)
_cell_measurement_reflns_used    5617
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.77
_cell_measurement_theta_min      2.17
_cell_volume                     2745.40(13)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0716
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37246
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_min         2.170
_exptl_absorpt_coefficient_mu    1.104
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Hexane'
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0560P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3907
_reflns_number_total             5004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc00412j2.cif
_cod_data_source_block           hsw41-1
_cod_depositor_comments
;Adding full bibliography for 1557749--1557750.cif.

 Adding full bibliography for 1557749--1557750.cif.
;
_cod_database_code               1557749
_shelxl_version_number           2014-3
_shelx_res_checksum              9775