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_4102671
_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_formula_moiety         'C28 H26 Br N2 O5'
_chemical_formula_sum            'C28 H26 Br N2 O5'
_chemical_formula_weight         550.42
_chemical_name_systematic
; 
 ? 
;
_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                 97.901(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.5013(9)
_cell_length_b                   6.8025(5)
_cell_length_c                   14.8285(12)
_cell_measurement_reflns_used    4116
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.34
_cell_measurement_theta_min      3.01
_cell_volume                     1249.05(16)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0816
_diffrn_reflns_av_sigmaI/netI    0.1334
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7595
_diffrn_reflns_theta_full        66.95
_diffrn_reflns_theta_max         66.95
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    2.594
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_correction_T_min  0.4235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             566
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.137
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1770
_refine_ls_R_factor_gt           0.1302
_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^)+(0.1644P)^2^+5.6254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3042
_refine_ls_wR_factor_ref         0.3356
_reflns_number_gt                2455
_reflns_number_total             4094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1032277_si_002.cif
_cod_data_source_block           x1001009
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4102671