Palladium-Catalyzed Regio-, Enantio-, and Diastereoselective Asymmetric [3 + 2] Cycloaddition Reactions: Synthesis of Chiral Cyclopentyl Phosphonates
Trost, Barry M.; Shinde, Anand H.; Wang, Youliang; Zuo, Zhijun; Min, Chang; ACS Catalysis  (2020) 1969–1975; doi:10.1021/acscatal.9b05073

data_4517340
_publ_section_title
;
 Palladium-Catalyzed Regio-, Enantio-, and Diastereoselective Asymmetric
 [3 + 2] Cycloaddition Reactions: Synthesis of Chiral Cyclopentyl
 Phosphonates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1969
_journal_page_last               1975
_journal_paper_doi               10.1021/acscatal.9b05073
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H22 N O7 P'
_chemical_formula_sum            'C25 H22 N O7 P'
_chemical_formula_weight         479.40
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                100.704(2)
_cell_angle_beta                 91.306(2)
_cell_angle_gamma                94.062(2)
_cell_formula_units_Z            1
_cell_length_a                   5.7494(6)
_cell_length_b                   9.6543(10)
_cell_length_c                   10.4417(11)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.32
_cell_measurement_theta_min      4.31
_cell_volume                     567.68(10)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14830
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.498
_diffrn_reflns_theta_min         4.312
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    1.487
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7513
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       rod
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.891
_refine_diff_density_min         -1.209
_refine_diff_density_rms         0.285
_refine_ls_abs_structure_details
;
 Flack x determined using 1600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1568P)^2^+0.7349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1898
_refine_ls_wR_factor_ref         0.2359
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                3752
_reflns_number_total             3828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b05073_si_002.cif
_cod_data_source_block           suahs301
_cod_depositor_comments          'Adding full bibliography for 4517340.cif.'
_cod_database_code               4517340
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.692
_shelx_estimated_absorpt_t_max   0.826
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              1750
_shelx_hkl_checksum              66088