Rhodium-catalyzed enantioselective addition of organoaluminum reagents to N-tosyl ketimines.
Hirner, Sebastian; Kolb, Andreas; Westmeier, Johannes; Gebhardt, Sandra; Middel, Stephen; Harms, Klaus; von Zezschwitz, Paultheo; Organic letters 16 (2014) 3162–3165; doi:10.1021/ol501372u

data_1516459
_publ_section_title
;
 Rhodium-catalyzed enantioselective addition of organoaluminum reagents to
 N-tosyl ketimines.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3162
_journal_page_last               3165
_journal_paper_doi               10.1021/ol501372u
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H21 N O2 S'
_chemical_formula_weight         327.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7947(4)
_cell_length_b                   9.9666(5)
_cell_length_c                   16.9986(7)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.1643
_cell_measurement_theta_min      2.3688
_cell_volume                     1659.40(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v3.0.31'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34221
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.204
_diffrn_reflns_theta_min         2.369
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 1486 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.021(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0306P)^2^+0.3803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0634
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3549
_reflns_number_total             3681
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501372u_si_001.cif
_cod_data_source_block           4a
_cod_depositor_comments
'Adding full bibliography for 1516457--1516460.cif.'
_cod_database_code               1516459
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.970
_shelxl_version_number           2013-4
_shelx_res_checksum              22386
_shelx_hkl_checksum              94294