Highly Enantioselective Organocatalytic Biginelli and Biginelli-Like Condensations: Reversal of the Stereochemistry by Tuning the 3,3'-Disubstituents of Phosphoric Acids
Nan Li; Xiao-Hua Chen; Jin Song; Shi-Wei Luo; Wu Fan; Liu-Zhu Gong; Journal of the American Chemical Society 131 (2009) 15301–15310; doi:10.1021/ja905320q

data_4105173
_publ_section_title
;
 Highly Enantioselective Organocatalytic Biginelli and Biginelli-Like
 Condensations: Reversal of the Stereochemistry by Tuning the
 3,3'-Disubstituents of Phosphoric Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15301
_journal_page_last               15310
_journal_paper_doi               10.1021/ja905320q
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H21 Br N2 S'
_chemical_formula_weight         401.36
_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                90.000(5)
_cell_angle_beta                 98.644(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   12.782(5)
_cell_length_b                   11.750(5)
_cell_length_c                   13.392(5)
_cell_measurement_reflns_used    9467
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      62.7463
_cell_measurement_theta_min      3.3299
_cell_volume                     1988.5(14)
_computing_cell_refinement       'CrysAlis RED'
_computing_data_collection       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'Ortep 3 (Louis J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24365
_diffrn_reflns_theta_full        62.81
_diffrn_reflns_theta_max         62.81
_diffrn_reflns_theta_min         3.34
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    3.807
_exptl_absorpt_correction_T_max  0.5164
_exptl_absorpt_correction_T_min  0.4376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.035(15)
_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     457
_refine_ls_number_reflns         6089
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0129P)^2^+0.8926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0676
_reflns_number_gt                4276
_reflns_number_total             6089
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja905320q_si_003.cif
_cod_data_source_block           081211-cu
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4105173