Synthesis of Both Enantiomers of a P-Chirogenic 1,2-Bisphospholanoethane Ligand via Convergent Routes and Application to Rhodium-Catalyzed Asymmetric Hydrogenation of CI-1008 (Pregabalin)
Garrett Hoge; Journal of the American Chemical Society 125 (2003) 10219–10227; doi:10.1021/ja034715o

data_4114082
_publ_section_title
;
 Synthesis of Both Enantiomers of a P-Chirogenic 1,2-Bisphospholanoethane
 Ligand via Convergent Routes and Application to Rhodium-Catalyzed
 Asymmetric Hydrogenation of CI-1008 (Pregabalin)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10219
_journal_page_last               10227
_journal_paper_doi               10.1021/ja034715o
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C31 H40 B F4 P2 Rh'
_chemical_formula_weight         664.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9304(9)
_cell_length_b                   15.0030(14)
_cell_length_c                   19.6514(18)
_cell_measurement_temperature    299(2)
_cell_volume                     2927.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      299(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22163
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.9101
_exptl_absorpt_correction_T_min  0.7419
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'deep red'
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       'regular col'
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_coef       0.0087(4)
_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   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         7272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                6487
_reflns_number_total             7272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja034715osi20030219_064820.cif
_cod_data_source_block           rh
_cod_database_code               4114082