Chiral Silver Complex-Catalyzed Diastereoselective and Enantioselective Michael Addition of 1-Pyrroline-5-carboxylates to α-Enones.
Koizumi, Akihiro; Harada, Masato; Haraguchi, Ryosuke; Fukuzawa, Shin-Ichi; The Journal of organic chemistry 82 (2017) 8927–8932; doi:10.1021/acs.joc.7b01335

data_4032709
_publ_section_title
;
 Chiral Silver Complex-Catalyzed Diastereoselective and Enantioselective
 Michael Addition of 1-Pyrroline-5-carboxylates to \a-Enones.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8927
_journal_page_last               8932
_journal_paper_doi               10.1021/acs.joc.7b01335
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H27 Fe N O3'
_chemical_formula_sum            'C26 H27 Fe N O3'
_chemical_formula_weight         457.35
_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                 94.060(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   6.0771(2)
_cell_length_b                   8.0868(3)
_cell_length_c                   21.8099(9)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.14
_cell_volume                     1069.14(7)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2015)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9872
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.139
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480.00
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.51
_refine_ls_abs_structure_details
;
 Flack x determined using 1813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+2.6900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                4500
_reflns_number_total             4779
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo7b01335_si_002.cif
_cod_data_source_block           C26H27FeNO3
_cod_database_code               4032709
_shelx_res_checksum              66044
_shelx_hkl_checksum              32484