Enantioselective Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofurans via a Cascade Allylboration/Oxo-Michael Reaction of o-Formyl Chalcones Catalyzed by a Chiral Phosphoric Acid.
Yang, Xing; Pang, Shuai; Cheng, Feng; Zhang, Yue; Lin, Ya-Wei; Yuan, Quan; Zhang, Fang-Lin; Huang, Yi-Yong; The Journal of organic chemistry 82 (2017) 10388–10397; doi:10.1021/acs.joc.7b01856

data_4032868
_publ_section_title
;
 Enantioselective Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofurans
 via a Cascade Allylboration/Oxo-Michael Reaction of o-Formyl Chalcones
 Catalyzed by a Chiral Phosphoric Acid.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10388
_journal_page_last               10397
_journal_paper_doi               10.1021/acs.joc.7b01856
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         323.33
_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'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.883(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.23(3)
_cell_length_b                   4.782(7)
_cell_length_c                   16.45(3)
_cell_measurement_reflns_used    554
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.75
_cell_measurement_theta_min      2.42
_cell_volume                     1658(5)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0881
_diffrn_reflns_av_unetI/netI     0.1383
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5660
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        24.982
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_min         1.933
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 313 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   3.1(10)
_refine_ls_extinction_coef       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1750
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0597P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1821
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                1234
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01856_si_002.cif
_cod_data_source_block           mo_170505c_0m
_cod_depositor_comments          'Adding full bibliography for 4032868.cif.'
_cod_original_cell_volume        1658(4)
_cod_database_code               4032868
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              77945
_shelx_hkl_checksum              44931