Asymmetric synthesis of functionalized trifluoromethyl-substituted pyrrolidines via an organocatalytic domino Michael/Mannich [3+2] cycloaddition.
Zhi, Ying; Zhao, Kun; Liu, Qiang; Wang, Ai; Enders, Dieter; Chemical communications (Cambridge, England) 52 (2016) 14011–14014; doi:10.1039/c6cc08352h

data_7125294
_publ_section_title
;
 Asymmetric synthesis of functionalized trifluoromethyl-substituted
 pyrrolidines via an organocatalytic domino Michael/Mannich [3+2]
 cycloaddition.
;
_journal_issue                   97
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14011
_journal_page_last               14014
_journal_paper_doi               10.1039/c6cc08352h
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 Br F3 N O6'
_chemical_formula_sum            'C21 H23 Br F3 N O6'
_chemical_formula_weight         522.31
_chemical_name_common            4h
_chemical_name_systematic        4h
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-10-17 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6647(6)
_cell_length_b                   15.3884(11)
_cell_length_c                   17.0772(12)
_cell_measurement_reflns_used    4748
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.39
_cell_volume                     2277.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35125
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.907
_diffrn_reflns_theta_min         1.781
_diffrn_source                   'Incoatec microsource'
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 2122 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.015(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         6794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0296P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0837
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                5571
_reflns_number_total             6794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08352h2.cif
_cod_data_source_block           4h
_cod_database_code               7125294
_shelx_estimated_absorpt_t_min   0.587
_shelx_estimated_absorpt_t_max   0.633
_shelxl_version_number           2013-2
_shelx_res_checksum              88873