A Chiral Sulfoxide-Ligated Ruthenium Complex for Asymmetric Catalysis: Enantio- and Regioselective Allylic Substitution
Barry M. Trost; Meera Rao; André P. Dieskau; Journal of the American Chemical Society 135 (2013) 18697–18704; doi:10.1021/ja411310w

data_4121302
_publ_contact_author_address
'Department of Chemistry, Stanford University'
_publ_contact_author_email       mrao2@stanford.edu
_publ_contact_author_name        'Meera Rao'
_publ_section_title
;
 A Chiral Sulfoxide-Ligated Ruthenium Complex for Asymmetric Catalysis:
 Enantio- and Regioselective Allylic Substitution
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18697
_journal_page_last               18704
_journal_paper_doi               10.1021/ja411310w
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H23 N2 O2 Ru S, P F6'
_chemical_formula_sum            'C19 H23 F6 N2 O2 P Ru S'
_chemical_formula_weight         589.49
_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_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                   6.6143(6)
_cell_length_b                   16.6130(15)
_cell_length_c                   20.6633(19)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.32
_cell_volume                     2270.6(4)
_computing_cell_refinement       'Bruker SAINT v8.18C'
_computing_data_collection       'Bruker APEX-II v2012-2.0'
_computing_data_reduction        'Bruker SAINT v8.18C'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  'Bruker TRIUMPH curved-graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31436
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+1.8793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0592
_reflns_number_gt                5169
_reflns_number_total             5365
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja411310w_si_002.cif
_cod_data_source_block           su1210
_cod_database_code               4121302