Development of Diamidophosphite Ligands and Their Application to the Palladium-Catalyzed Vinyl-Substituted Trimethylenemethane Asymmetric [3 + 2] Cycloaddition
Barry M. Trost; Tom M. Lam; Journal of the American Chemical Society 134 (2012) 11319–11321; doi:10.1021/ja305717r

data_4118279
_publ_contact_author_address     'Department of Chemistry, 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
;
 Development of Diamidophosphite Ligands and Their Application to the
 Palladium-Catalyzed Vinyl-Substituted Trimethylenemethane Asymmetric [3 +
 2] Cycloaddition
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11319
_journal_page_last               11321
_journal_paper_doi               10.1021/ja305717r
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H21 Cl N2 O'
_chemical_formula_sum            'C24 H21 Cl N2 O'
_chemical_formula_weight         388.88
_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                 99.679(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1987(5)
_cell_length_b                   6.0777(3)
_cell_length_c                   16.6677(8)
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      69.41
_cell_measurement_theta_min      2.69
_cell_volume                     1018.43(9)
_computing_cell_refinement       'Bruker SAINT v7.66A'
_computing_data_collection       'Bruker APEX-II v2010-7'
_computing_data_reduction        'Bruker SAINT v7.66A'
_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 0.991
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9810
_diffrn_reflns_theta_full        69.64
_diffrn_reflns_theta_max         69.64
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  0.8855
_exptl_absorpt_correction_T_min  0.5259
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       blade
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1451 Friedel Pairs measured'
_refine_ls_abs_structure_Flack   0.018(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0434P)^2^+0.1906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                3370
_reflns_number_total             3570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305717r_si_003.cif
_cod_data_source_block           su1205
_cod_database_code               4118279