Double diastereocontrol in bifunctional thiourea organocatalysis: iterative Michael-Michael-Henry sequence regulated by the configuration of chiral catalysts.
Varga, Szilárd; Jakab, Gergely; Drahos, László; Holczbauer, Tamás; Czugler, Mátyás; Soós, Tibor; Organic letters 13 (2011) 5416–5419; doi:10.1021/ol201559j

data_1502325
_publ_section_title
;
 Double diastereocontrol in bifunctional thiourea organocatalysis:
 iterative Michael-Michael-Henry sequence regulated by the configuration
 of chiral catalysts.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5416
_journal_page_last               5419
_journal_paper_doi               10.1021/ol201559j
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 N2 O5, 2(C H4 O)'
_chemical_formula_sum            'C26 H30 N2 O7'
_chemical_formula_weight         482.52
_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                   6.02250(10)
_cell_length_b                   19.0267(4)
_cell_length_c                   21.5818(4)
_cell_measurement_reflns_used    17922
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      71.88
_cell_measurement_theta_min      6.58
_cell_volume                     2473.02(8)
_computing_cell_refinement       'CrystalClear v1.4.0 (Rigaku, 2008)'
_computing_data_collection       'CrystalClear v1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear v1.4.0 (Rigaku, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku R-Axis RAPID'
_diffrn_measurement_method       '\w -scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23638
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         6.58
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear v1.4.0 (Rigaku, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0634P)^2^+1.5567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                2774
_reflns_number_total             4262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201559j_si_002.cif
_cod_data_source_block           ma8d
_cod_database_code               1502325