Cinchona-Based Primary Amine-Catalyzed Asymmetric Cascade Aza-Michael-Aldol Reactions of Enones with 2-(1H-Pyrrol-2-yl)-2-oxoacetates: Synthesis of Chiral Pyrrolizines with Multistereocenters
Hyo-Jun Lee; Chang-Woo Cho; Journal of Organic Chemistry 78 (2013) 3306–3312; doi:10.1021/jo4001614

data_4028123
_publ_section_title
;
 Cinchona-Based Primary Amine-Catalyzed Asymmetric Cascade
 Aza-Michael-Aldol Reactions of Enones with
 2-(1H-Pyrrol-2-yl)-2-oxoacetates: Synthesis of Chiral Pyrrolizines with
 Multistereocenters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3306
_journal_page_last               3312
_journal_paper_doi               10.1021/jo4001614
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 Br2 N2 O5'
_chemical_formula_sum            'C18 H18 Br2 N2 O5'
_chemical_formula_weight         502.16
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9911(7)
_cell_length_b                   10.4994(7)
_cell_length_c                   18.8049(13)
_cell_measurement_reflns_used    4963
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.22
_cell_volume                     1972.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14536
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        <2.0
_exptl_absorpt_coefficient_mu    4.141
_exptl_absorpt_correction_T_max  0.4768
_exptl_absorpt_correction_T_min  0.3697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.925
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+2.6590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                2933
_reflns_number_total             4858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4001614_si_002.cif
_cod_data_source_block           CCWNo2-ma
_cod_database_code               4028123