Catalytic Enantioselective Silylation of N-Sulfonylimines: Asymmetric Synthesis of α-Amino Acids from CO2 via Stereospecific Carboxylation of α-Amino Silanes.
Mita, Tsuyoshi; Sugawara, Masumi; Saito, Keisuke; Sato, Yoshihiro; Organic letters 16 (2014) 3028–3031; doi:10.1021/ol501143c

data_1516135
_publ_section_title
;
 Catalytic Enantioselective Silylation of N-Sulfonylimines: Asymmetric
 Synthesis of \a-Amino Acids from CO2 via Stereospecific Carboxylation of
 \a-Amino Silanes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3028
_journal_page_last               3031
_journal_paper_doi               10.1021/ol501143c
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C14 H25 N O2 S Sn'
_chemical_formula_sum            'C14 H25 N O2 S Sn'
_chemical_formula_weight         390.11
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.738(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.1188(3)
_cell_length_b                   10.5531(3)
_cell_length_c                   15.6491(5)
_cell_measurement_reflns_used    17132
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.38
_cell_volume                     1717.26(13)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2013)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16969
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.608
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792.00
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.30
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3074 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.008(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0170
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0273P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0434
_reflns_number_gt                4048
_reflns_number_total             7206
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol501143c_si_003.cif
_cod_data_source_block           SX236
_cod_depositor_comments
'Adding full bibliography for 1516134--1516135.cif.'
_cod_database_code               1516135