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_4024734
_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         'C31 H50 N1 O3 S1 Sn1'
_chemical_formula_sum            'C31 H50 N O3 S Sn'
_chemical_formula_weight         635.5
_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                   8.2236(7)
_cell_length_b                   20.444(3)
_cell_length_c                   38.045(5)
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      6.4
_cell_volume                     6396.3(14)
_computing_publication_material
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_computing_structure_refinement
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_max 0.9816
_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  0.1447
_diffrn_reflns_av_sigmaI/netI    0.0918
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            64556
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         6.4
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  0.9501
_exptl_absorpt_correction_T_min  0.8317
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'Jana2006  (Petricek, Dusek & Palatinus, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3195(3)
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             2664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.74
_refine_diff_density_min         -1.88
_refine_ls_abs_structure_details
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    2.10
_refine_ls_goodness_of_fit_ref   1.93
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    400
_refine_ls_number_parameters     662
_refine_ls_number_reflns         18153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.0982
_refine_ls_shift/su_max          0.0338
_refine_ls_shift/su_mean         0.0012
_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          0.1648
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                12972
_reflns_number_total             18153
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo900223k_si_001.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        'C31 H50 N1 O3 S1 Sn1'
_cod_database_code               4024734