Palladium-catalyzed asymmetric allylic amination: enantioselective synthesis of chiral α-methylene substituted β-aminophosphonates
Wang, Xubin; Wang, Xiaoming; Han, Zhaobin; Wang, Zheng; Ding, Kuiling; Organic Chemistry Frontiers 4 (2017) 271–; doi:10.1039/C6QO00597G

data_1553574
_publ_section_title
;
 Palladium-catalyzed asymmetric allylic amination: enantioselective
 synthesis of chiral \a-methylene substituted \b-aminophosphonates
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              271
_journal_paper_doi               10.1039/C6QO00597G
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H23 Br N O3 P'
_chemical_formula_weight         424.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-07-08 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8916(7)
_cell_length_b                   26.4389(19)
_cell_length_c                   7.7778(6)
_cell_measurement_reflns_used    5660
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.57
_cell_volume                     2034.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20495
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.535
_diffrn_reflns_theta_min         1.540
_exptl_absorpt_coefficient_mu    2.116
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.535
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
; 
 Flack x determined using 1804 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.024(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.096
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.7163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4962
_reflns_number_total             6186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00597g2.cif
_cod_data_source_block           dm14071
_cod_database_code               1553574
_shelx_estimated_absorpt_t_min   0.569
_shelx_estimated_absorpt_t_max   0.816
_shelxl_version_number           2013-4
_shelx_res_checksum              26709
_shelx_hkl_checksum              40950