A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade.
Cheng, Tao; Meng, Sixuan; Huang, Yong; Organic letters 15 (2013) 1958–1961; doi:10.1021/ol4006129

data_1511932
_publ_section_title
;
 A Highly Diastereoselective and Enantioselective Synthesis of
 Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic
 Resolution Cascade.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1958
_journal_page_last               1961
_journal_paper_doi               10.1021/ol4006129
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H24 N2 O6 S'
_chemical_formula_sum            'C21 H24 N2 O6 S'
_chemical_formula_weight         432.48
_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                   7.72840(10)
_cell_length_b                   13.4661(3)
_cell_length_c                   20.7179(14)
_cell_measurement_reflns_used    13130
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      69.00
_cell_measurement_theta_min      6.60
_cell_volume                     2156.14(16)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3841
_diffrn_reflns_theta_full        69.00
_diffrn_reflns_theta_max         69.00
_diffrn_reflns_theta_min         6.57
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_T_max  0.7302
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 1562 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.017(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0567P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                3381
_reflns_number_total             3835
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol4006129_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               1511932