Phosphine-Catalyzed Enantioselective [4 + 2] Annulation of o-Quinone Methides with Allene Ketones
Wang, Zhen; Wang, Tianli; Yao, Weijun; Lu, Yixin; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01936

data_1546560
_publ_section_title
;
 Phosphine-Catalyzed Enantioselective [4 + 2] Annulation of o-Quinone
 Methides with Allene Ketones
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01936
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H26 O7'
_chemical_formula_sum            'C29 H26 O7'
_chemical_formula_weight         486.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 101.793(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2281(5)
_cell_length_b                   9.6521(5)
_cell_length_c                   24.3706(11)
_cell_measurement_reflns_used    1202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.439
_cell_measurement_theta_min      3.705
_cell_volume                     2585.4(2)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2015.5.2'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2015.5.2'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30162
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.439
_diffrn_reflns_theta_min         3.705
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.03(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         10058
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+1.0132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                9340
_reflns_number_total             10058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01936_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               1546560
_shelx_estimated_absorpt_t_min   0.823
_shelx_estimated_absorpt_t_max   0.879
_shelxl_version_number           2014/6
_shelx_res_checksum              62002
_shelx_hkl_checksum              8658