Cinchona-Based Primary Amine Catalyzed a Proximal Functionalization of Dienamines: Asymmetric α-Fluorination of α-Branched Enals
Arimitsu, Satoru; Yonamine, Tsunaki; Higashi, Masahiro; ACS Catalysis  (2017) 4736–; doi:10.1021/acscatal.7b01178

data_4514155
_publ_section_title
;
 Cinchona-Based Primary Amine Catalyzed a Proximal Functionalization of
 Dienamines: Asymmetric \a-Fluorination of \a-Branched Enals
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              4736
_journal_paper_doi               10.1021/acscatal.7b01178
_journal_year                    2017
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C25 H22 Br2 F N O'
_chemical_formula_sum            'C25 H22 Br2 F N O'
_chemical_formula_weight         531.26
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.995(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   13.4096(4)
_cell_length_b                   5.2499(2)
_cell_length_c                   16.5010(6)
_cell_measurement_reflns_used    8863
_cell_measurement_temperature    123
_cell_measurement_theta_max      71.88
_cell_measurement_theta_min      3.44
_cell_volume                     1110.93(7)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11215
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_min         3.446
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.835
_exptl_absorpt_correction_T_max  0.713
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             532.00
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         1.24
_refine_diff_density_min         -1.29
_refine_ls_abs_structure_details
;
 Flack x determined using 678 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0483P)^2^+1.3329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.879
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                2627
_reflns_number_total             3837
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs7b01178_si_002.cif
_cod_data_source_block           yona4Br
_cod_database_code               4514155
_shelx_res_checksum              99731
_shelx_hkl_checksum              54253