Stereospecific Coupling of H-Phosphinates and Secondary Phosphine Oxides with Amines and Alcohols: A General Method for the Preparation of Optically Active Organophosphorus Acid Derivatives
Gang Wang; Ruwei Shen; Qing Xu; Midori Goto; Yufen Zhao; Li-Biao Han; Journal of Organic Chemistry 75 (2010) 3890–3892; doi:10.1021/jo100473s

data_4025456
_publ_section_title
;
 Stereospecific Coupling of H-Phosphinates and Secondary Phosphine Oxides
 with Amines and Alcohols: A General Method for the Preparation of
 Optically Active Organophosphorus Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3890
_journal_page_last               3892
_journal_paper_doi               10.1021/jo100473s
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C16 H24 N O2 P'
_chemical_formula_weight         293.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.186(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6140(10)
_cell_length_b                   5.7613(7)
_cell_length_c                   16.5693(19)
_cell_measurement_reflns_used    4278
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      29.192
_cell_measurement_theta_min      2.363
_cell_volume                     821.03(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating unit'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4939
_diffrn_reflns_theta_full        26.22
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  254
_diffrn_standards_number         133
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0806P)^2^+0.1150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                3337
_reflns_number_total             3386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100473s_si_001.cif
_cod_data_source_block           han3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025456