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_4024737
_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         'C28 H51 N1 O3 S1 Sn1'
_chemical_formula_sum            'C28 H51 N O3 S Sn'
_chemical_formula_weight         600.5
_chemical_name_systematic        ' ?'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           'Jana2006 Version : 24/10/2007'
_cell_angle_alpha                90
_cell_angle_beta                 90.175(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4125(18)
_cell_length_b                   8.1024(6)
_cell_length_c                   24.215(2)
_cell_measurement_temperature    100
_cell_measurement_theta_max      32
_cell_measurement_theta_min      6.41
_cell_volume                     3023.9(5)
_computing_publication_material
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_computing_structure_refinement
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 98.5
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            58916
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         6.41
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'(Jana2006; Petricek, Dusek & Palatinus, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.3186
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.22
_refine_diff_density_min         -0.44
_refine_ls_abs_structure_details
'Jana2006 (Petricek, Dusek & Palatinus, 2006)'
_refine_ls_abs_structure_Flack   0.027(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    1.31
_refine_ls_goodness_of_fit_ref   1.32
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     624
_refine_ls_number_reflns         20184
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.0017
_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          0.0947
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                17792
_reflns_number_total             20184
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo900223k_si_004.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        'C28 H51 N1 O3 S1 Sn1'
_cod_database_code               4024737