Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes
Gianna Reginato; Bernardo Pezzati; Andrea Ienco; Gabriele Manca; Andrea Rossin; Alessandro Mordini; Journal of Organic Chemistry 76 (2011) 7415–7422; doi:10.1021/jo2010878

data_4026571
_publ_contact_author_address     'ICCOM-CNR, Firenze (Italy)'
_publ_contact_author_email       a.ienco@iccom.cnr.it
_publ_contact_author_fax         39(055)5225203
_publ_contact_author_name        'Ienco, Andrea'
_publ_contact_author_phone       39(055)5225284
_publ_section_title
;
 Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from
 Acyclic Chiral Amino Allylsilanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7415
_journal_page_last               7422
_journal_paper_doi               10.1021/jo2010878
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H26 N2 O4 S1'
_chemical_formula_sum            'C20 H26 N2 O4 S'
_chemical_formula_weight         390.49
_space_group_IT_number           19
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_atom_sites_solution_hydrogens   geom
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_audit_creation_method           'WinGX routine CIF_UPDATE'
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_cell_length_b                   14.306(1)
_cell_length_c                   19.458(2)
_cell_measurement_reflns_used    3914
_cell_measurement_temperature    293(2)
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        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
;
_computing_data_collection
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        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
;
_computing_data_reduction
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        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.4547
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0283871055
_diffrn_orient_matrix_UB_12      -0.0406156512
_diffrn_orient_matrix_UB_13      -0.0175326595
_diffrn_orient_matrix_UB_21      -0.0020607295
_diffrn_orient_matrix_UB_22      -0.0247413304
_diffrn_orient_matrix_UB_23      0.0315673886
_diffrn_orient_matrix_UB_31      -0.0857106101
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_diffrn_orient_matrix_UB_33      0.0048889336
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
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_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         4.19
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.56898
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_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
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        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       prism
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_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.813
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.104
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2254
_reflns_number_total             5183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2010878_si_001_2.cif
_cod_data_source_block           c3b
_cod_original_cell_volume        2184.3(2)
_cod_database_code               4026571