Zn-ProPhenol Catalyzed Enantio- and Diastereoselective Direct Vinylogous Mannich Reactions between α,β- and β,γ-Butenolides and Aldimines.
Trost, Barry M.; Gnanamani, Elumalai; Tracy, Jacob S.; Kalnmals, Christopher A.; Journal of the American Chemical Society 139 (2017) 18198–18201; doi:10.1021/jacs.7b11361

data_4131825
_publ_section_title
;
 Zn-ProPhenol Catalyzed Enantio- and Diastereoselective Direct Vinylogous
 Mannich Reactions between \a,\b- and \b,\g-Butenolides and Aldimines.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18198
_journal_page_last               18201
_journal_paper_doi               10.1021/jacs.7b11361
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H22 F N O4'
_chemical_formula_sum            'C23 H22 F N O4'
_chemical_formula_weight         395.41
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0224(2)
_cell_length_b                   11.4699(4)
_cell_length_c                   24.6868(8)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.12
_cell_measurement_theta_min      3.58
_cell_volume                     1988.43(11)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            37274
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.176
_diffrn_reflns_theta_min         3.581
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_correction_T_min  0.8987
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       rod
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0423P)^2^+0.2436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0681
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3858
_reflns_number_total             3923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11361_si_002.cif
_cod_data_source_block           su1710
_cod_database_code               4131825
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.942
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              67955
_shelx_hkl_checksum              17433