Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system
Suga, Hiroyuki; Yoshiwara, Masahiro; Yamaguchi, Takaaki; Bando, Takashi; Taguchi, Mizuki; Inaba, Ayano; Goto, Yuichi; Kikuchi, Ayaka; Itoh, Kennosuke; Toda, Yasunori; Chemical Communications  (2019) –; doi:10.1039/C8CC09224A

data_7122742
_publ_section_title
;
 Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric
 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual
 catalytic system
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09224A
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_sum            'C25 H26 Br N3 O5'
_chemical_formula_weight         528.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc20yk8t
_audit_update_record
;
2018-10-26 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.436(7)
_cell_length_b                   13.238(12)
_cell_length_c                   25.73(2)
_cell_measurement_reflns_used    177
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      20.2243
_cell_measurement_theta_min      3.1454
_cell_volume                     2533(4)
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13792
_diffrn_reflns_theta_full        26.94
_diffrn_reflns_theta_max         26.94
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    1.662
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_correction_T_min  0.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.209
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.466
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                3612
_reflns_number_total             5376
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc09224a2.cif
_cod_data_source_block           I
_cod_original_cell_volume        2533.(4)
_cod_database_code               7122742