Synthesis of P-Stereogenic Compounds via Kinetic Deprotonation and Dynamic Thermodynamic Resolution of Phosphine Sulfides: Opposite Sense of Induction Using (-)-Sparteine
Jonathan J. Gammon; Viktoria H. Gessner; Greg R. Barker; Johan Granander; Adrian C. Whitwood; Carsten Strohmann; Peter O'Brien; Brian Kelly; Journal of the American Chemical Society 132 (2010) 13922–13927; doi:10.1021/ja1060966

data_4103167
_publ_contact_author_address
;Department of Chemistry
University of York
Heslington
York
YO10 5DD
;
_publ_contact_author_email       paob1@york.ac.uk
_publ_contact_author_name        'Prof Peter O'Brien'
_publ_section_title
;
 Synthesis of P-Stereogenic Compounds via Kinetic Deprotonation and
 Dynamic Thermodynamic Resolution of Phosphine Sulfides: Opposite Sense of
 Induction Using (-)-Sparteine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13922
_journal_page_last               13927
_journal_paper_doi               10.1021/ja1060966
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H25 O P S'
_chemical_formula_sum            'C11 H25 O P S'
_chemical_formula_weight         236.34
_chemical_name_systematic
(RP,RC)-1-(t-Butylmethylphosphinothioyl)-3,3-dimethylbutan-2-ol
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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                 93.8920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2989(3)
_cell_length_b                   10.8750(5)
_cell_length_c                   20.2407(10)
_cell_measurement_reflns_used    8979
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      29.86
_cell_measurement_theta_min      2.75
_cell_volume                     1383.30(11)
_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, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15597
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.02
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         7825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.0912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0670
_reflns_number_gt                7521
_reflns_number_total             7825
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1060966_si_003.cif
_cod_data_source_block           pob0705a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4103167