Enantioselective Formal Aza-Diels-Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas
Mathieu P. Lalonde; Meredeth A. McGowan; Naomi S. Rajapaksa; Eric N. Jacobsen; Journal of the American Chemical Society 135 (2013) 1891–1894; doi:10.1021/ja310718f

data_4119265
_publ_section_title
;
 Enantioselective Formal Aza-Diels-Alder Reactions of Enones with Cyclic
 Imines Catalyzed by Primary Aminothioureas
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1891
_journal_page_last               1894
_journal_paper_doi               10.1021/ja310718f
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C28 H25 Br N2 O3 S . 0.5(C6 H6)'
_chemical_formula_moiety         'C28 H25 Br N2 O3 S, 0.5(C6 H6)'
_chemical_formula_structural     '(C28 H25 Br N2 O3 S) 0.5(C6 H6)'
_chemical_formula_sum            'C31 H28 Br N2 O3 S'
_chemical_formula_weight         588.52
_chemical_name_common            MPL-X-119#2
_chemical_name_systematic
; 
(4S,12bS)-4-(4-Bromophenyl)-12-tosyl-1,3,4,6,7,12b-hexahydro-
indolo[2,3-a]quinolizin-2(12H)-one Hemi(benzene) Solvate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
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_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.981(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1356(1)
_cell_length_b                   24.0863(4)
_cell_length_c                   14.2335(2)
_cell_measurement_reflns_used    6379
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      22.02
_cell_measurement_theta_min      2.23
_cell_volume                     2738.08(7)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction
;
SAINT V7.34A (Bruker AXS, 2006b), SADABS (Bruker AXS, 2004)
;
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
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_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1492 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0846
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30492
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.613
_exptl_absorpt_correction_T_max  0.9237
_exptl_absorpt_correction_T_min  0.7824
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_coef       0.0020(4)
_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   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     742
_refine_ls_number_reflns         9649
_refine_ls_number_restraints     223
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0417
_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^)
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                7739
_reflns_number_total             9649
_reflns_threshold_expression     I>2\s(I)
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_cod_data_source_block           4ae
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4119265