Highly enantioselective organocatalyzed vinylogous Michael-type reaction for the construction of trifluoromethylated all-carbon quaternary stereocenters.
Chen, Qiao; Wang, Guoqiang; Jiang, Xianxing; Xu, Zhaoqing; Lin, Li; Wang, Rui; Organic letters 16 (2014) 1394–1397; doi:10.1021/ol500157b

data_1513816
_publ_section_title
;
 Highly enantioselective organocatalyzed vinylogous Michael-type reaction
 for the construction of trifluoromethylated all-carbon quaternary
 stereocenters.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1394
_journal_page_last               1397
_journal_paper_doi               10.1021/ol500157b
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C20 H20 Cl F3 N2 O5'
_chemical_formula_weight         460.83
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2bc 2'
_space_group_name_H-M_alt        'P 2 21 21'
_symmetry_space_group_name_Hall  'P 2bc 2'
_symmetry_space_group_name_H-M   'P 2 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6488(11)
_cell_length_b                   16.8386(13)
_cell_length_c                   17.9210(19)
_cell_measurement_temperature    293(2)
_cell_volume                     2308.1(4)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_unetI/netI     0.1377
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7371
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_min         3.320
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_platon_squeeze_details
;
;
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_extinction_coef       0.032(10)
_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   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1738
_refine_ls_R_factor_gt           0.1035
_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^)+(0.1785P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2653
_refine_ls_wR_factor_ref         0.3379
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                1833
_reflns_number_total             4289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol500157b_si_002.cif
_cod_data_source_block           chenqiao1126
_cod_original_cell_volume        2308.1(5)
_cod_database_code               1513816
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.941
_shelxl_version_number           2013-2
_shelx_res_checksum              69410
_shelx_hkl_checksum              4756