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_1546561
_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         'C24 H20 O5 S'
_chemical_formula_sum            'C24 H20 O5 S'
_chemical_formula_weight         420.46
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.621(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4465(3)
_cell_length_b                   12.4107(7)
_cell_length_c                   14.8394(9)
_cell_measurement_reflns_used    1548
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.313
_cell_measurement_theta_min      2.140
_cell_volume                     1002.02(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 Bruker '
_diffrn_measurement_method       'omega/2theta scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            46026
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.313
_diffrn_reflns_theta_min         2.140
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.279
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 3546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         9671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.0946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                8381
_reflns_number_total             9671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01936_si_003.cif
_cod_data_source_block           F570
_cod_database_code               1546561
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.947
_shelx_res_checksum              1107
_shelx_hkl_checksum              82570