Dynamic Kinetic Asymmetric Synthesis of Substituted Pyrrolidines from Racemic Cyclopropanes and Aldimines: Reaction Development and Mechanistic Insights
Andrew T. Parsons; Austin G. Smith; Andrew J. Neel; Jeffrey S. Johnson; Journal of the American Chemical Society 132 (2010) 9688–9692; doi:10.1021/ja1032277

data_4102670
_publ_section_title
;
 Dynamic Kinetic Asymmetric Synthesis of Substituted Pyrrolidines from
 Racemic Cyclopropanes and Aldimines: Reaction Development and Mechanistic
 Insights
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9688
_journal_page_last               9692
_journal_paper_doi               10.1021/ja1032277
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H27 N O5'
_chemical_formula_sum            'C28 H27 N O5'
_chemical_formula_weight         457.51
_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   difmap
_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                   8.8298(2)
_cell_length_b                   11.8871(3)
_cell_length_c                   21.7347(6)
_cell_measurement_reflns_used    5929
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.93
_cell_measurement_theta_min      4.07
_cell_volume                     2281.29(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27470
_diffrn_reflns_theta_full        70.05
_diffrn_reflns_theta_max         70.05
_diffrn_reflns_theta_min         4.07
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.9472
_exptl_absorpt_correction_T_min  0.8950
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker-AXS Apex2 Numerical'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0490P)^2^+0.1563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                3841
_reflns_number_total             4230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1032277_si_001.cif
_cod_data_source_block           x0910008
_cod_database_code               4102670