Diastereoselective Three-Component Vinylogous Mannich Reaction of Nitrogen Heterocycles, Acyl/Sulfonyl Chlorides, and Silyloxyfurans/pyrroles.
Janody, Simon; Hermange, Philippe; Retailleau, Pascal; Thierry, Josiane; Dodd, Robert H.; The Journal of organic chemistry 79 (2014) 5673–5683; doi:10.1021/jo500827j

data_4029609
_publ_section_title
;
 Diastereoselective Three-Component Vinylogous Mannich Reaction of
 Nitrogen Heterocycles, Acyl/Sulfonyl Chlorides, and
 Silyloxyfurans/pyrroles.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5673
_journal_page_last               5683
_journal_paper_doi               10.1021/jo500827j
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C24 H24 N2 O4, C Cl3 D'
_chemical_formula_sum            'C25 H24 Cl3 D N2 O4'
_chemical_formula_weight         524.82
_chemical_name_systematic
; 
(R)-tert-butyl 2-((R)-5-acetyl-5,6-dihydrophenanthridin-6-yl)-
5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate compound with 
deuterated chloroform (1:1) 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 132.200(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.2117(18)
_cell_length_b                   9.1944(4)
_cell_length_c                   23.1388(16)
_cell_measurement_reflns_used    4546
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8
_cell_measurement_theta_min      2.1
_cell_volume                     5076.7(9)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 300.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 18
               Slice: 22.0000 - 112.0000
         Image width: 5.0000
            Exp time: 300.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 18
               Slice: 42.0000 - 132.0000
         Image width: 5.0000
            Exp time: 300.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000

;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.031786
_diffrn_orient_matrix_UB_12      -0.097561
_diffrn_orient_matrix_UB_13      -0.028723
_diffrn_orient_matrix_UB_21      0.061612
_diffrn_orient_matrix_UB_22      -0.080301
_diffrn_orient_matrix_UB_23      0.027619
_diffrn_orient_matrix_UB_31      -0.078128
_diffrn_orient_matrix_UB_32      -0.023634
_diffrn_orient_matrix_UB_33      0.024725
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10748
_diffrn_reflns_theta_full        68.14
_diffrn_reflns_theta_max         68.14
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    3.553
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00053(8)
_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   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1881
_reflns_number_gt                2432
_reflns_number_total             4462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500827j_si_001.cif
_cod_data_source_block           SJ351_A
_cod_depositor_comments
'Adding full bibliography for 4029606--4029611.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4029609