Asymmetric synthesis of amines by the Knochel-type MgCl2-enhanced addition of benzyl zinc reagents to N-tert-butanesulfinyl aldimines.
Buesking, Andrew W.; Baguley, Tyler D.; Ellman, Jonathan A.; Organic letters 13 (2011) 964–967; doi:10.1021/ol103002t

data_1501951
_publ_section_title
;
 Asymmetric synthesis of amines by the Knochel-type MgCl2-enhanced
 addition of benzyl zinc reagents to N-tert-butanesulfinyl aldimines.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              964
_journal_page_last               967
_journal_paper_doi               10.1021/ol103002t
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'S F O N C16 H26'
_chemical_formula_sum            'C16 H26 F N O S'
_chemical_formula_weight         299.45
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.7454(2)
_cell_length_b                   10.5113(3)
_cell_length_c                   18.0667(13)
_cell_measurement_reflns_used    4177
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      4.87
_cell_volume                     1660.79(13)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.882
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6921
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.782
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648.00
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.570
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  959 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       0.0029(7)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0769
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0827P)^2^+0.3304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2081
_reflns_number_gt                1620
_reflns_number_total             2687
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol103002t_si_002.cif
_cod_data_source_block           '_tb01'
_cod_original_formula_sum        'S F O N C16 H26'
_cod_database_code               1501951