Asymmetric Organocatalytic Three-Component 1,3-Dipolar Cycloaddition: Control of Stereochemistry via a Chiral Brønsted Acid Activated Dipole
Xiao-Hua Chen; Wen-Quan Zhang; Liu-Zhu Gong; Journal of the American Chemical Society 130 (2008) 5652–5653; doi:10.1021/ja801034e

data_4107731
_publ_section_title
;
 Asymmetric Organocatalytic Three-Component 1,3-Dipolar Cycloaddition:
 Control of Stereochemistry via a Chiral Br\/onsted Acid Activated Dipole
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5652
_journal_page_last               5653
_journal_paper_doi               10.1021/ja801034e
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C20 H24 Br N O8'
_chemical_formula_sum            'C20 H24 Br N O8'
_chemical_formula_weight         486.31
_chemical_name_common            none
_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                   11.4513(5)
_cell_length_b                   12.4207(8)
_cell_length_c                   15.2454(6)
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      2.1
_cell_volume                     2168.40(19)
_computing_cell_refinement       'Bruker SMART '
_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT+ (Bruker, 2001)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7574
_diffrn_reflns_theta_full        26.65
_diffrn_reflns_theta_max         26.65
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    1.941
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2538
_reflns_number_total             4137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja801034e-file001.cif
_cod_data_source_block           080121a
_cod_database_code               4107731