Catalytic Asymmetric Synthesis of Quaternary Trifluoromethyl α- to ϵ-Amino Acid Derivatives via Umpolung Allylation/2-aza-Cope Rearrangement
Sun, Xi-Shang; Wang, Xing-Heng; Tao, Hai-Yan; Wei, Liang; Wang, Chun-Jiang; Chemical Science  (2020) –; doi:10.1039/D0SC04685J

data_1559112
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Quaternary Trifluoromethyl \a- to
 &#x03F5;-Amino Acid Derivatives via Umpolung Allylation/2-aza-Cope
 Rearrangement
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04685J
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H25 F3 N2 O3'
_chemical_formula_weight         446.46
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2020-07-22 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.74(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.227(5)
_cell_length_b                   15.501(5)
_cell_length_c                   12.834(4)
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      61.40
_cell_measurement_theta_min      3.68
_cell_volume                     2389.8(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14495
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        63.259
_diffrn_reflns_theta_max         63.259
_diffrn_reflns_theta_min         3.505
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         6479
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0693P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1475
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.695
_reflns_Friedel_fraction_max     0.695
_reflns_number_gt                4356
_reflns_number_total             6479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04685j2.cif
_cod_data_source_block           x_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        2390.0(15)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1559112
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              46003