Potassium tert-butoxide mediated stereoselective/direct Mannich reaction of α-substituted-γ-lactams with in situ generated aryl N-silyl imines
Casselman, Tyler D.; Madhusudhanan, Mithun C.; Mai, Binh Khanh; Liu, Peng; Stoltz, Brian M.; Chemical Science 16 (2025) 9863–9871; doi:10.1039/D4SC06391K

data_1574554
_publ_section_title
;
 Potassium tert-butoxide mediated stereoselective/direct Mannich reaction
 of \a-substituted-\g-lactams with in situ generated aryl N-silyl imines
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              9863
_journal_page_last               9871
_journal_paper_doi               10.1039/D4SC06391K
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C27 H27 Br N2 O2'
_chemical_formula_weight         491.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-30 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.083(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8500(11)
_cell_length_b                   49.858(4)
_cell_length_c                   8.0771(10)
_cell_measurement_reflns_used    9071
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.40
_cell_measurement_theta_min      3.55
_cell_volume                     4772.1(8)
_computing_cell_refinement       'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_data_collection       'APEX3 v2019.1-0 (Bruker Nano, 2019)'
_computing_data_reduction        'SAINT v8.40A (Bruker-AXS, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 7.69
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       62
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            75046
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.545
_diffrn_reflns_theta_min         3.546
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.548
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.211
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         9652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0679
_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^)+(0.0469P)^2^+11.4189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8681
_reflns_number_total             9652
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06391k2.cif
_cod_data_source_block           V20240
_cod_depositor_comments
'Adding full bibliography for 1574553--1574555.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574554
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.515
_shelx_estimated_absorpt_t_max   0.883
_shelx_res_checksum              56389