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_1574553
_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            'C21 H23 Br N2 O2'
_chemical_formula_weight         415.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                 93.651(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.430(3)
_cell_length_b                   9.489(2)
_cell_length_c                   21.189(5)
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.33
_cell_measurement_theta_min      2.31
_cell_volume                     1892.2(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      100(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 KAPPA'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            53031
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.430
_diffrn_reflns_theta_min         1.926
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.190
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.5241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
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_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         9140
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.7206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7953
_reflns_number_total             9140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06391k2.cif
_cod_data_source_block           D21009
_cod_depositor_comments
'Adding full bibliography for 1574553--1574555.cif.'
_cod_original_cell_volume        1892.2(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1574553
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.407
_shelx_estimated_absorpt_t_max   0.560
_shelx_res_checksum              69372