Synthesis of Highly Enantioenriched Chiral α-Aminoorganotins via Diastereoselective Ring Opening of Chiral N-(Arenesulfonyl) 2-Tributylstannyloxazolidines
Vincent Coeffard; Erwan Le Grognec; Isabelle Beaudet; Michel Evain; Jean-Paul Quintard; Journal of Organic Chemistry 74 (2009) 5822–5838; doi:10.1021/jo900223k

data_4024735
_publ_contact_author_address
; Institut des Mat\'eriaux Jean Rouxel
  UMR CNRS 6502
  Universit\'e de Nantes,
  Facult\'e des Sciences et des Techniques
  2 rue de la Houssini\`ere
  BP 32229
  44322 NANTES CEDEX 3
  FRANCE
;
_publ_contact_author_email       Michel.Evain@univ-nantes.fr
_publ_contact_author_fax         '(33) 02 40 37 39 95'
_publ_contact_author_name        'Pr. Michel Evain'
_publ_contact_author_phone       '(33) 02 40 37 39 23'
_publ_section_title
;
Synthesis of Highly Enantioenriched Chiral \a-Aminoorganotins via
Diastereoselective Ring Opening of Chiral N-(Arenesulfonyl)
2-Tributylstannyloxazolidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5822
_journal_page_last               5838
_journal_paper_doi               10.1021/jo900223k
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H47 N1 O3 S1 Sn1'
_chemical_formula_sum            'C30 H47 N O3 S Sn'
_chemical_formula_weight         620.5
_chemical_name_systematic        ' ?'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           'Jana2006 Version : 24/10/2007'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.8641(7)
_cell_length_b                   20.288(2)
_cell_length_c                   38.732(3)
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      6.40
_cell_volume                     6179.6(10)
_computing_publication_material
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_computing_structure_refinement
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Nonius CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            65402
_diffrn_reflns_theta_full        29.52
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         6.40
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'(Jana2006; Petricek, Dusek & Palatinus, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3334
_exptl_crystal_description       'thick needle'
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.6
_refine_diff_density_min         -0.41
_refine_ls_abs_structure_details
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_refine_ls_abs_structure_Flack   0.029(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    1.39
_refine_ls_goodness_of_fit_ref   1.40
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     655
_refine_ls_number_reflns         17153
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.0078
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(\s^2^(I)+0.001936I^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                15537
_reflns_number_total             17153
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo900223k_si_002.cif
_cod_data_source_block           (I)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C30 H47 N1 O3 S1 Sn1'
_cod_database_code               4024735