Enantioselective Hydrophosphonylation of in Situ Generated N-Acyl Ketimines Catalyzed by BINOL-Derived Phosphoric Acid.
Suneja, Arun; Unhale, Rajshekhar A.; Singh, Vinod K.; Organic letters 19 (2017) 476–479; doi:10.1021/acs.orglett.6b03623

data_1545029
_publ_section_title
;
 Enantioselective Hydrophosphonylation of in Situ Generated N-Acyl
 Ketimines Catalyzed by BINOL-Derived Phosphoric Acid.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              476
_journal_page_last               479
_journal_paper_doi               10.1021/acs.orglett.6b03623
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H24 N O5.5 P'
_chemical_formula_weight         397.37
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                92.181(4)
_cell_angle_beta                 98.685(4)
_cell_angle_gamma                106.652(3)
_cell_formula_units_Z            4
_cell_length_a                   8.8456(7)
_cell_length_b                   13.4959(12)
_cell_length_c                   17.5870(17)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.35
_cell_volume                     1981.1(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_number            7380
_diffrn_reflns_point_group_measured_fraction_full 0.500
_diffrn_reflns_point_group_measured_fraction_max 0.500
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.352
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       Rod
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.451
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.15(10)
_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     981
_refine_ls_number_reflns         7380
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0509P)^2^+2.7481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                6644
_reflns_number_total             7380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03623_si_002.cif
_cod_data_source_block           6b
_cod_depositor_comments          'Adding full bibliography for 1545029.cif.'
_cod_original_formula_sum        'C20 H24 N O5.50 P'
_cod_database_code               1545029
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              50420
_shelx_hkl_checksum              18698