Enantioselective Construction of Pyrrolidines by Palladium-Catalyzed Asymmetric [3 + 2] Cycloaddition of Trimethylenemethane with Imines
Barry M. Trost; Steven M. Silverman; Journal of the American Chemical Society 134 (2012) 4941–4954; doi:10.1021/ja210981a

data_4117639
_publ_contact_author_address     'Dept. of Chemistry, Stanford University'
_publ_contact_author_email       ssilverman@stanford.edu
_publ_contact_author_name        'Steve Silverman'
_publ_contact_author_phone       '858 761 2799'
_publ_section_title
;
 Enantioselective Construction of Pyrrolidines by Palladium-Catalyzed
 Asymmetric [3 + 2] Cycloaddition of Trimethylenemethane with Imines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4941
_journal_page_last               4954
_journal_paper_doi               10.1021/ja210981a
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H18 N2 O4 S'
_chemical_formula_sum            'C20 H18 N2 O4 S'
_chemical_formula_weight         382.42
_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                   9.8098(2)
_cell_length_b                   10.8229(2)
_cell_length_c                   17.5387(3)
_cell_measurement_reflns_used    5960
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.05
_cell_measurement_theta_min      4.80
_cell_volume                     1862.09(6)
_computing_cell_refinement       'Bruker SAINT v7.66A'
_computing_data_collection       'Bruker APEX-II v2009-9'
_computing_data_reduction        'Bruker SAINT v7.66A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'combination of \w and \f-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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10414
_diffrn_reflns_theta_full        61.53
_diffrn_reflns_theta_max         61.53
_diffrn_reflns_theta_min         4.80
_exptl_absorpt_coefficient_mu    1.792
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7439
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       tablet
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0501P)^2^+0.2062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                2619
_reflns_number_total             2768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja210981a_si_003.cif
_cod_data_source_block           su026
_cod_database_code               4117639