Regio- and Enantioselective Synthesis of Pyrrolidines Bearing a Quaternary Center by Palladium-Catalyzed Asymmetric [3 + 2] Cycloaddition of Trimethylenemethanes
Barry M. Trost; Tom M. Lam; Melissa A. Herbage; Journal of the American Chemical Society 135 (2013) 2459–2461; doi:10.1021/ja312351s

data_4119370
_publ_contact_author_address     'Department of CHemisty, Stanford University'
_publ_contact_author_email       tommtlam@stanford.edu
_publ_contact_author_name        'Tom Lam'
_publ_contact_author_phone       '650 723 1100'
_publ_section_title
;
 Regio- and Enantioselective Synthesis of Pyrrolidines Bearing a
 Quaternary Center by Palladium-Catalyzed Asymmetric [3 + 2] Cycloaddition
 of Trimethylenemethanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2459
_journal_page_last               2461
_journal_paper_doi               10.1021/ja312351s
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H26 N2 O3 S'
_chemical_formula_sum            'C23 H26 N2 O3 S'
_chemical_formula_weight         410.52
_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                   6.5589(3)
_cell_length_b                   15.8671(6)
_cell_length_c                   20.7298(8)
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.28
_cell_measurement_theta_min      7.03
_cell_volume                     2157.37(15)
_computing_cell_refinement       'Bruker SAINT v8.18C'
_computing_data_collection       'Bruker APEX-II v2012-2.0'
_computing_data_reduction        'Bruker SAINT v8.18C'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  'MONTEL Multi-layer'
_diffrn_radiation_source         'Incoatec micro-focus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17857
_diffrn_reflns_theta_full        71.28
_diffrn_reflns_theta_max         71.28
_diffrn_reflns_theta_min         7.03
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(10)
_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     266
_refine_ls_number_reflns         4110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.2549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0725
_reflns_number_gt                4036
_reflns_number_total             4110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja312351s_si_003.cif
_cod_data_source_block           su1212
_cod_database_code               4119370