Enantioselective desymmetrization of diphenylphosphinamides via (-)-sparteine-mediated ortho-lithiation. Synthesis of P-chiral ligands.
Popovici, Cristinel; Oña-Burgos, Pascual; Fernández, Ignacio; Roces, Laura; García-Granda, Santiago; Iglesias, María José; López Ortiz, Fernando; Organic letters 12 (2010) 428–431; doi:10.1021/ol902545q

data_1503353
_publ_section_title
;
 Enantioselective desymmetrization of diphenylphosphinamides via
 (-)-sparteine-mediated ortho-lithiation. Synthesis of P-chiral ligands.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              428
_journal_page_last               431
_journal_paper_doi               10.1021/ol902545q
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H24 N1 O2 P1'
_chemical_formula_sum            'C19 H24 N O2 P'
_chemical_formula_weight         329.36
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-04-21T13:17:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.57890(10)
_cell_length_b                   15.4126(2)
_cell_length_c                   15.8221(3)
_cell_measurement_reflns_used    3442
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.4291
_cell_measurement_theta_min      4.0059
_cell_measurement_wavelength     1.54184
_cell_volume                     1848.19(5)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
        (compiled Sep 15 2009,11:49:04)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF-99 (Beurskens et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0827
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_UB_11      -0.0156318618
_diffrn_orient_matrix_UB_12      0.0121328719
_diffrn_orient_matrix_UB_13      0.096242748
_diffrn_orient_matrix_UB_21      -0.1902187001
_diffrn_orient_matrix_UB_22      0.0326941243
_diffrn_orient_matrix_UB_23      -0.0109306734
_diffrn_orient_matrix_UB_31      -0.068381683
_diffrn_orient_matrix_UB_32      -0.0936505219
_diffrn_orient_matrix_UB_33      0.0085932301
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0877
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9109
_diffrn_reflns_theta_full        65.45
_diffrn_reflns_theta_max         65.45
_diffrn_reflns_theta_min         4
_exptl_absorpt_coefficient_mu    1.382
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
XABS2        
Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
Cubic fit to sin(theta)/lambda - 24 parameters
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                2427
_reflns_number_total             3136
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902545q_si_002.cif
_cod_data_source_block           c122f1
_cod_database_code               1503353