Highly enantioselective three-component direct mannich reactions of unfunctionalized ketones catalyzed by bifunctional organocatalysts.
Guo, Qunsheng; Zhao, John Cong-Gui; Organic letters 15 (2013) 508–511; doi:10.1021/ol303315c

data_1508876
_publ_section_title
;
 Highly enantioselective three-component direct mannich reactions of
 unfunctionalized ketones catalyzed by bifunctional organocatalysts.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              508
_journal_page_last               511
_journal_paper_doi               10.1021/ol303315c
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H24 Br N O3 S'
_chemical_formula_sum            'C28 H24 Br N O3 S'
_chemical_formula_weight         534.45
_chemical_name_systematic
; 
(2<i>S</i>, 3<i>S</i>)-1-(4-Bromophenyl)-2,3-diphenyl
-3-(tosylamino)propan-1-one
;
_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                 92.756(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.676(4)
_cell_length_b                   5.7270(12)
_cell_length_c                   23.637(5)
_cell_measurement_reflns_used    10051
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.0
_cell_measurement_theta_min      2.6
_cell_volume                     2390.0(9)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17709
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.839
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 3035 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.013(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         9057
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0450P)^2^+0.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                8179
_reflns_number_total             9057
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303315c_si_002.cif
_cod_data_source_block           bdtpo
_cod_database_code               1508876