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_1501950
_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 O4 N C21 H27'
_chemical_formula_sum            'C21 H27 N O4 S'
_chemical_formula_weight         389.51
_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                   5.57254(10)
_cell_length_b                   11.2226(2)
_cell_length_c                   32.524(2)
_cell_measurement_reflns_used    7085
_cell_measurement_temperature    93
_cell_measurement_theta_max      65.44
_cell_measurement_theta_min      6.72
_cell_volume                     2034.00(14)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_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 11.111
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            8763
_diffrn_reflns_theta_full        65.91
_diffrn_reflns_theta_max         65.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.626
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             832.00
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.370
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1309 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0691
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1169P)^2^+0.1423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2016
_reflns_number_gt                2672
_reflns_number_total             3351
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol103002t_si_001.cif
_cod_data_source_block           '_tb02'
_cod_original_cell_volume        2034.02(15)
_cod_original_formula_sum        'S O4 N C21 H27'
_cod_database_code               1501950