Three-component reactions of sulfonylimidates, silyl glyoxylates and N-tert-butanesulfinyl aldimines: an efficient, diastereoselective, and enantioselective synthesis of Cyclic N-sulfonylamidines.
Yao, Ming; Lu, Chong-Dao; Organic letters 13 (2011) 2782–2785; doi:10.1021/ol201029b

data_1502227
_publ_section_title
;
 Three-component reactions of sulfonylimidates, silyl glyoxylates and
 N-tert-butanesulfinyl aldimines: an efficient, diastereoselective, and
 enantioselective synthesis of Cyclic N-sulfonylamidines.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2782
_journal_page_last               2785
_journal_paper_doi               10.1021/ol201029b
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C26 H38 N2 O6 S2 Si'
_chemical_formula_weight         566.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.575(4)
_cell_angle_beta                 96.749(4)
_cell_angle_gamma                103.098(4)
_cell_formula_units_Z            2
_cell_length_a                   9.071(3)
_cell_length_b                   13.012(5)
_cell_length_c                   13.847(5)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.35
_cell_volume                     1505.4(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9097
_diffrn_reflns_theta_full        27.18
_diffrn_reflns_theta_max         27.18
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9723
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0053(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+1.5600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.1963
_reflns_number_gt                3612
_reflns_number_total             6458
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201029b_si_003.cif
_cod_data_source_block           lu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1505.5(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502227