Stereoselective Synthesis of Densely Functionalized Pyrrolidin-2-ones by a Conjugate Addition/Nitro-Mannich/Lactamization Reaction
James C. Anderson; Lisa R. Horsfall; Andreas S. Kalogirou; Matthew R. Mills; Gregory J. Stepney; Graham J. Tizzard; Journal of Organic Chemistry 77 (2012) 6186–6198; doi:10.1021/jo301000r

data_4027333
_publ_section_title
;
 Stereoselective Synthesis of Densely Functionalized Pyrrolidin-2-ones by
 a Conjugate Addition/Nitro-Mannich/Lactamization Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6186
_journal_page_last               6198
_journal_paper_doi               10.1021/jo301000r
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H19 F3 N2 O3 S'
_chemical_formula_sum            'C19 H19 F3 N2 O3 S'
_chemical_formula_weight         412.42
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.33990(10)
_cell_length_b                   10.16140(10)
_cell_length_c                   22.2832(15)
_cell_measurement_reflns_used    7495
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.4
_cell_measurement_theta_min      2.0
_cell_volume                     1888.39(13)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn944+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7566
_diffrn_reflns_theta_full        66.37
_diffrn_reflns_theta_max         66.37
_diffrn_reflns_theta_min         6.63
_exptl_absorpt_coefficient_mu    2.000
_exptl_absorpt_correction_T_max  0.7402
_exptl_absorpt_correction_T_min  0.6244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       'Cut Block'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.173
_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   0.011(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0248
_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^)+(0.0289P)^2^+0.2955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0637
_reflns_number_gt                3039
_reflns_number_total             3114
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo301000r_si_003.cif
_cod_data_source_block           2011ncs0214aa
_cod_database_code               4027333