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_4028422
_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         'C27 H34 B O6 P'
_chemical_formula_sum            'C27 H34 B O6 P'
_chemical_formula_weight         496.32
_chemical_name_systematic
; 
(2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)
-2-borane-2-methoxy-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.853(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0937(10)
_cell_length_b                   10.0847(9)
_cell_length_c                   12.7293(11)
_cell_measurement_reflns_used    1879
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7
_cell_measurement_theta_min      3.6
_cell_volume                     1369.9(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 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_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  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5461
_diffrn_reflns_theta_full        58.97
_diffrn_reflns_theta_max         58.97
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    1.196
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       stick
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881;1118 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_coef       0.0049(8)
_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   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0746P)^2^+0.3494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.2010
_reflns_number_gt                1913
_reflns_number_total             3168
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400864s_si_002_2.cif
_cod_data_source_block           248
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028422