Amide phosphonium salt catalyzed enantioselective Mannich addition of isoxazole-based nucleophiles to β,γ-alkynyl-α-ketimino esters.
Gu, Congzheng; Tian, Guangzheng; Yin, Qingyu; Wu, Fan; Li, Zhiming; Wu, Xiaoyu; Organic & biomolecular chemistry 20 (2022) 3323–3334; doi:10.1039/d2ob00309k

data_7158596
_publ_section_title
;
 Amide phosphonium salt catalyzed enantioselective Mannich addition of
 isoxazole-based nucleophiles to \b,\g-alkynyl-\a-ketimino esters.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3323
_journal_page_last               3334
_journal_paper_doi               10.1039/d2ob00309k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_sum            'C30 H24 Br N3 O7'
_chemical_formula_weight         618.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2021-09-20 deposited with the CCDC.	2022-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4017(3)
_cell_length_b                   18.1121(5)
_cell_length_c                   18.3977(5)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      66.66
_cell_measurement_theta_min      2.44
_cell_volume                     3132.84(16)
_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      150.(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'Bruker D8 VENTURE DUO PHOTON III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios MX Multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22259
_diffrn_reflns_theta_full        66.67
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_min         2.44
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec Ius 3.0'
_exptl_absorpt_coefficient_mu    2.191
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_platon_squeeze_details
;
;
_refine_diff_density_max         1.712
_refine_diff_density_min         -0.402
_refine_ls_abs_structure_details
;

Flack x determined using 2208 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(6)
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5261
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0600
_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^)+(0.1119P)^2^+0.8529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1578
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                5123
_reflns_number_total             5261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00309k2.cif
_cod_data_source_block           20210120c
_cod_depositor_comments          'Adding full bibliography for 7158596.cif.'
_cod_database_code               7158596
_shelx_res_checksum              25311