Enantioselective synthesis of quaternary α-aminophosphonates by Pd-catalyzed arylation of cyclic α-ketiminophosphonates with arylboronic acids.
Yan, Zhong; Wu, Bo; Gao, Xiang; Zhou, Yong-Gui; Chemical communications (Cambridge, England) 52 (2016) 10882–10885; doi:10.1039/c6cc04096a

data_7124712
_publ_section_title
;
 Enantioselective synthesis of quaternary \a-aminophosphonates by
 Pd-catalyzed arylation of cyclic \a-ketiminophosphonates with arylboronic
 acids.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10882
_journal_page_last               10885
_journal_paper_doi               10.1039/c6cc04096a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H24 N O6 P S'
_chemical_formula_weight         425.42
_chemical_name_systematic
(S)-Diisopropyl(2,2-dioxido-4-phenyl-3,4-dihydrobenzo[e][1,2,3]oxathiazin-4-yl)phosphonate
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-03-19 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   9.7393(12)
_cell_length_b                   9.7393(12)
_cell_length_c                   18.532(3)
_cell_measurement_reflns_used    3373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.703
_cell_measurement_theta_min      4.829
_cell_volume                     1522.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9161
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.415
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 1652 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3927
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0504P)^2^+0.0703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.974
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3701
_reflns_number_total             3927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc04096a2.cif
_cod_data_source_block           cd15294
_cod_original_cell_volume        1522.3(5)
_cod_database_code               7124712
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
_shelx_res_checksum              76338