Highly Diastereoselective Switchable Enantioselective Mannich Reaction of Glycine Derivatives with Imines
Xiao-Xia Yan; Qian Peng; Qing Li; Kai Zhang; Jun Yao; Xue-Long Hou; Yun-Dong Wu; Journal of the American Chemical Society 130 (2008) 14362–14363; doi:10.1021/ja804527r

data_4108579
_publ_section_title
;
 Highly Diastereoselective Switchable Enantioselective Mannich Reaction of
 Glycine Derivatives with Imines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14362
_journal_page_last               14363
_journal_paper_doi               10.1021/ja804527r
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H27 Br N2 O4 S'
_chemical_formula_weight         591.51
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 92.638(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.636(5)
_cell_length_b                   9.558(4)
_cell_length_c                   13.761(6)
_cell_measurement_reflns_used    998
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.900
_cell_measurement_theta_min      4.736
_cell_volume                     1397.4(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '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  0.1215
_diffrn_reflns_av_sigmaI/netI    0.1806
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7324
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75334
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.864
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0698
_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^)+(0.0824P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                2266
_reflns_number_total             4476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja804527r_si_003.cif
_cod_data_source_block           cd28101
_cod_original_cell_volume        1397.4(10)
_cod_database_code               4108579