Construction of three contiguous stereocenters through amine-catalyzed asymmetric aldol reactions.
Hikawa, Ryoga; Shimogaki, Mio; Kano, Taichi; Chemical communications (Cambridge, England) 59 (2023) 8424–8427; doi:10.1039/d3cc01606d

data_7131825
_publ_section_title
;
 Construction of three contiguous stereocenters through amine-catalyzed
 asymmetric aldol reactions.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8424
_journal_page_last               8427
_journal_paper_doi               10.1039/d3cc01606d
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_sum            'C15 H31 Br O3 Si'
_chemical_formula_weight         367.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-07-12 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.594(7)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   13.5084(3)
_cell_length_b                   8.30240(10)
_cell_length_c                   26.1715(5)
_cell_measurement_reflns_used    33768
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      3.35
_cell_volume                     2864.57(12)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            33091
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.177
_diffrn_reflns_theta_min         3.352
_exptl_absorpt_coefficient_mu    3.571
_exptl_absorpt_correction_T_max  0.149
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1164
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane hexane'
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.429
_exptl_crystal_size_min          0.400
_refine_diff_density_max         2.012
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.210
_refine_ls_abs_structure_details
;
 Flack x determined using 4240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         10061
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0544P)^2^+0.0551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                9887
_reflns_number_total             10061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01606d2.cif
_cod_data_source_block           yg0128_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7131825
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              436
_shelx_hkl_checksum              81834