Asymmetric Carbamoyl Anion Additions to Chiral N-Phosphonyl Imines via the GAP Chemistry Process and Stereoselectivity Enrichments.
Seifert, Cole W.; Pindi, Suresh; Li, Guigen; The Journal of organic chemistry 80 (2014) 447–; doi:10.1021/jo5024443

data_4030316
_publ_section_title
;
 Asymmetric Carbamoyl Anion Additions to Chiral N-Phosphonyl Imines via
 the GAP Chemistry Process and Stereoselectivity Enrichments.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              447
_journal_paper_doi               10.1021/jo5024443
_journal_volume                  80
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H39 N4 O3 P'
_chemical_formula_weight         462.56
_chemical_name_systematic
;
(S)-2-(((3aR,7aR)-1,3-diisopropyl-2-oxidohexahydro-1H-benzo[d][1,3,2]
diazaphosphol-2(3H)-yl)amino)-1-morhpolino-2-phenylethanone
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-07T08:23:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.7890(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2564(3)
_cell_length_b                   11.0884(4)
_cell_length_c                   11.8407(4)
_cell_measurement_reflns_used    7037
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.52
_cell_volume                     1212.66(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11205
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         2.205
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       balde
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details
;
 Flack x determined using 1574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.1551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0718
_reflns_number_gt                4278
_reflns_number_total             4489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5024443_si_001.cif
_cod_data_source_block           5c
_cod_depositor_comments          'Adding full bibliography for 4030316.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4030316
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2014-3
_shelx_res_checksum              38375
_shelx_hkl_checksum              80554