An organocatalytic direct Mannich-cyclization cascade as [3+2] annulation: asymmetric synthesis of 2,3-substituted pyrrolidines
Indresh Kumar; Nisar A. Mir; Vivek K. Gupta; Rajnikant; Chem.Commun. 48 (2012) 6975–; doi:10.1039/c2cc33103a

data_7107956
_publ_section_title
;
 An organocatalytic direct Mannich-cyclization cascade as [3+2]
 annulation: asymmetric synthesis of 2,3-substituted pyrrolidines
;
_journal_name_full               Chem.Commun.
_journal_page_first              6975
_journal_paper_doi               10.1039/c2cc33103a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C18 H20 N2 O4'
_chemical_formula_sum            'C18 H20 N2 O4'
_chemical_formula_weight         328.36
_chemical_name_systematic
;
((2S,3S)-1-(4-methoxyphenyl)-2-(3-nitrophenyl)
pyrrolidin-3-yl)methanol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 95.224(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2761(4)
_cell_length_b                   7.6312(5)
_cell_length_c                   14.6614(10)
_cell_measurement_reflns_used    4103
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0804
_cell_measurement_theta_min      3.7698
_cell_volume                     810.70(9)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisRed (Oxford Diffraction,2010)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  PLATON(Spek,2009)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '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  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15385
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crysalisPro
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(15)
_refine_ls_extinction_coef       0.033(3)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0418P)^2^+0.0176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                2266
_reflns_number_total             3157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc33103a.txt
_cod_data_source_block           indresh3
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7107956