Asymmetric Phase-Transfer-Catalyzed Conjugate Addition of Glycine Imine to Exocyclic α,β-Unsaturated Ketones: Construction of Polycyclic Imines Containing Three Stereocenters
Jing Nie; Ming-Qing Hua; Heng-Ying Xiong; Yan Zheng; Jun-An Ma; Journal of Organic Chemistry 77 (2012) 4209–4216; doi:10.1021/jo300500r

data_4027183
_publ_section_title
;
 Asymmetric Phase-Transfer-Catalyzed Conjugate Addition of Glycine Imine
 to Exocyclic \a,\b-Unsaturated Ketones: Construction of Polycyclic Imines
 Containing Three Stereocenters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4209
_journal_page_last               4216
_journal_paper_doi               10.1021/jo300500r
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C31 H32 Br Cl2 N O3'
_chemical_formula_weight         617.39
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_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.543(12)
_cell_length_b                   10.960(13)
_cell_length_c                   27.61(3)
_cell_measurement_reflns_used    4845
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2888(6)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  RigakuMercury375R
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1480
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            25626
_diffrn_reflns_theta_full        27.68
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    1.642
_exptl_absorpt_correction_T_max  0.7792
_exptl_absorpt_correction_T_min  0.5973
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.140
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_coef       0.051(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.301
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.1261
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3521
_refine_ls_wR_factor_ref         0.3733
_reflns_number_gt                2307
_reflns_number_total             3765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300500r_si_002.cif
_cod_data_source_block           110301a
_cod_original_cell_volume        2887(6)
_cod_database_code               4027183