Design of Chiral Bis-phosphoric Acid Catalyst Derived from (R)-3,3'-Di(2-hydroxy-3-arylphenyl)binaphthol: Catalytic Enantioselective Diels-Alder Reaction of α,β-Unsaturated Aldehydes with Amidodienes
Norie Momiyama; Tohru Konno; Yuichi Furiya; Takeaki Iwamoto; Masahiro Terada; Journal of the American Chemical Society 133 (2011) 19294–19297; doi:10.1021/ja2081444

data_4107179
_publ_section_title
;
 Design of Chiral Bis-phosphoric Acid Catalyst Derived from
 (R)-3,3'-Di(2-hydroxy-3-arylphenyl)binaphthol: Catalytic Enantioselective
 Diels-Alder Reaction of \a,\b-Unsaturated Aldehydes with Amidodienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19294
_journal_page_last               19297
_journal_paper_doi               10.1021/ja2081444
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C45 H30 Cl2 O8 P2'
_chemical_formula_weight         831.53
_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                 99.947(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.735(4)
_cell_length_b                   15.966(8)
_cell_length_c                   13.967(7)
_cell_measurement_reflns_used    4855
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.37
_cell_volume                     1918.6(16)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_sigmaI/netI    0.0977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17840
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.8359
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         6741
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0422P)^2^+1.1605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                5465
_reflns_number_total             6741
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2081444_si_002.cif
_cod_data_source_block           terada01
_cod_original_cell_volume        1918.5(16)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4107179