Alternative Synthesis of P-Chiral Phosphonite-Borane Complexes: Application to the Synthesis of Phostone-Phostone Dimers
Angélique Ferry; Gaëlle Malik; Pascal Retailleau; Xavier Guinchard; David Crich; Journal of Organic Chemistry 78 (2013) 6858–6867; doi:10.1021/jo400864s

data_4028421
_publ_contact_author_address
;Centre de Recherches de Gif
Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email       xavier.guinchard@icsn.cnrs-gif.fr
_publ_contact_author_fax         +33169077247
_publ_contact_author_name
;
'Guinchard, Xavier'
;
_publ_contact_author_phone       +33169823011
_publ_section_title
;
 Alternative Synthesis of P-Chiral Phosphonite-Borane Complexes:
 Application to the Synthesis of Phostone-Phostone Dimers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6858
_journal_page_last               6867
_journal_paper_doi               10.1021/jo400864s
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H36 B O6 P'
_chemical_formula_sum            'C28 H36 B O6 P'
_chemical_formula_weight         510.35
_chemical_name_systematic
; 
(2S,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)
-2-borane-2-ethoxy-1,2-oxaphosphinan-3-ol 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.076(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0993(11)
_cell_length_b                   9.4276(9)
_cell_length_c                   14.6656(11)
_cell_measurement_reflns_used    2153
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.6
_cell_measurement_theta_min      3.0
_cell_volume                     1396.3(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 34
               Slice: 24.0000 - 194.0000
         Image width: 5.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 9
               Slice: 20.0000 - 65.0000
         Image width: 5.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000

;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.051748
_diffrn_orient_matrix_UB_12      0.036098
_diffrn_orient_matrix_UB_13      -0.053349
_diffrn_orient_matrix_UB_21      0.084414
_diffrn_orient_matrix_UB_22      0.023146
_diffrn_orient_matrix_UB_23      -0.032309
_diffrn_orient_matrix_UB_31      0.000885
_diffrn_orient_matrix_UB_32      -0.097017
_diffrn_orient_matrix_UB_33      -0.027558
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10547
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881;1555 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0061(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4189
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.1509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                3652
_reflns_number_total             4189
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400864s_si_002_1.cif
_cod_data_source_block           xg-312
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028421