Construction of an all-carbon quaternary stereocenter by organocatalytic enantioselective alpha-functionalization of alpha-substituted beta-ketocarbonyls with electron deficient vinylarenes
Shizhou Liu; Mengchao Tong; Yang Yu; Hexin Xie; Hao Li; Wei Wang; Chem.Commun. 51 (2015) 11221–; doi:10.1039/C5cc03562G

data_7117401
_publ_section_title
;
 Construction of an all-carbon quaternary stereocenter by organocatalytic
 enantioselective alpha-functionalization of alpha-substituted
 beta-ketocarbonyls with electron deficient vinylarenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              11221
_journal_paper_doi               10.1039/C5cc03562G
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H23 N O7 S'
_chemical_formula_weight         397.43
_chemical_name_systematic
; 
 ? 
;
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-03-26 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.249(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5125(13)
_cell_length_b                   13.887(2)
_cell_length_c                   14.680(2)
_cell_measurement_reflns_used    4384
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.874
_cell_measurement_theta_min      5.093
_cell_volume                     1939.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11823
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         1.387
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 2619 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         7463
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0751P)^2^+0.0827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.877
_reflns_friedel_fraction_full    0.963
_reflns_friedel_fraction_max     0.957
_reflns_number_gt                6389
_reflns_number_total             7463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc03562g2.cif
_cod_data_source_block           cd214673
_cod_database_code               7117401
_shelxl_version_number           2013-4
_shelx_res_checksum              15352
_shelx_hkl_checksum              22445