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_4103166
_publ_contact_author_address
;
Anorganische Chemie
Technische Universitaet Dortmund
Otto-Hahn-Strasse 6
44227 Dortmund
Germany
;
_publ_contact_author_email       carsten.strohmann@tu-dortmund.de
_publ_contact_author_fax         '0049 231 755-3807'
_publ_contact_author_name        'Carsten Strohmann'
_publ_contact_author_phone       '0049 231 755-7062'
_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_sum            'C21 H40 Li N2 P S'
_chemical_formula_weight         390.52
_chemical_name_systematic
;
 ?
;
_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_date             2009-09-10T13:30:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5593(8)
_cell_length_b                   11.6886(8)
_cell_length_c                   33.860(2)
_cell_measurement_temperature    173(2)
_cell_volume                     4574.9(5)
_computing_cell_refinement       'SAINTPLUS 6.02 (Bruker AXS, 1999)'
_computing_data_collection       'SMART 5.622 (Bruker AXS, 2001)'
_computing_data_reduction        'SAINTPLUS 6.02 (Bruker AXS, 1999)'
_computing_molecular_graphics    'Ortep-3 V1.073 (Farrugia, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX-CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            69378
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         1.2
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9342
_exptl_absorpt_correction_T_min  0.8971
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2.01 (Bruker AXS, 1999)'
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         9973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0641P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                9117
_reflns_number_total             9973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1060966_si_002.cif
_cod_data_source_block           vi190708
_cod_original_cell_volume        4574.9(6)
_cod_database_code               4103166