Asymmetric Cascade Annulation Based on Enantioselective Oxa-Diels-Alder Cycloaddition of in Situ Generated Isochromenyliums by Cooperative Binary Catalysis of Pd(OAc)2 and (S)-Trip
Shu-Yan Yu; Hao Zhang; Yang Gao; Lei Mo; Shaozhong Wang; Zhu-Jun Yao; Journal of the American Chemical Society 135 (2013) 11402–11407; doi:10.1021/ja405764p

data_4120228
_publ_section_title
;
 Asymmetric Cascade Annulation Based on Enantioselective Oxa-Diels-Alder
 Cycloaddition of in Situ Generated Isochromenyliums by Cooperative Binary
 Catalysis of Pd(OAc)2 and (S)-Trip
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11402
_journal_page_last               11407
_journal_paper_doi               10.1021/ja405764p
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H32 O4'
_chemical_formula_sum            'C31 H32 O4'
_chemical_formula_weight         468.57
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   13.1073(19)
_cell_length_b                   13.1073(19)
_cell_length_c                   12.630(3)
_cell_measurement_reflns_used    6705
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.04
_cell_measurement_theta_min      3.50
_cell_volume                     1879.1(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7324
_diffrn_reflns_theta_full        66.95
_diffrn_reflns_theta_max         66.95
_diffrn_reflns_theta_min         3.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.21(14)
_refine_ls_extinction_coef       0.0079(5)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0437P)^2^+0.1588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                3570
_reflns_number_total             3582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja405764p_si_003.cif
_cod_data_source_block           120
_cod_original_cell_volume        1879.1(5)
_cod_database_code               4120228