Efficient synthesis of chiral cyclic acetals by metal and Bronsted acid co-catalyzed enantioselective four-component cascade reactions
Lin Qiu; Xin Guo; Chaoqun Ma; Huang Qiu; Shunying Liu; Liping Yang; Wenhao Hu; Chem.Commun. 50 (2014) 2196–; doi:10.1039/c3cc49063g

data_7111985
_publ_section_title
;
 Efficient synthesis of chiral cyclic acetals by metal and Bronsted acid
 co-catalyzed enantioselective four-component cascade reactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              2196
_journal_paper_doi               10.1039/c3cc49063g
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H23 Br2 N O6'
_chemical_formula_weight         605.27
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8142(7)
_cell_length_b                   14.0221(8)
_cell_length_c                   15.3593(9)
_cell_measurement_temperature    296(2)
_cell_volume                     2544.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29563
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    3.227
_exptl_absorpt_correction_T_max  0.5943
_exptl_absorpt_correction_T_min  0.3443
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+1.0440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                3826
_reflns_number_total             4478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc49063g.txt
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7111985