Intramolecular Sulfur Transfer in N-Enoyl Oxazolidine-2-thiones Promoted by Brønsted Acids. Practical Asymmetric Synthesis of β-Mercapto Carboxylic Acids and Mechanistic Insights
Claudio Palomo; Mikel Oiarbide; Rosa López; Pedro B. González; Enrique Gómez-Bengoa; José M. Saá; Anthony Linden; Journal of the American Chemical Society 128 (2006) 15236–15247; doi:10.1021/ja0654027

data_4111146
_publ_section_title
;
 Intramolecular Sulfur Transfer in N-Enoyl Oxazolidine-2-thiones Promoted
 by Br\/onsted Acids. Practical Asymmetric Synthesis of \b-Mercapto
 Carboxylic Acids and Mechanistic Insights
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15236
_journal_page_last               15247
_journal_paper_doi               10.1021/ja0654027
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H16 Cl N O2 S '
_chemical_formula_sum            'C10 H16 Cl N O2 S'
_chemical_formula_weight         249.75
_chemical_melting_point          329
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   6.8389(1)
_cell_length_b                   8.3595(1)
_cell_length_c                   21.7120(3)
_cell_measurement_reflns_used    47218
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     1241.27(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'TEXCIF (Linden, 1999)'
_computing_structure_refinement
'teXsan (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SIR92 direct methods (Altomare et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1.723
_diffrn_measured_fraction_theta_max 1.723
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '?\w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32525
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.38
_refine_ls_abs_structure_details 'Flack & Bernardinelli (2000)'
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   2.4820
_refine_ls_goodness_of_fit_ref   2.4420
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/[^2^(F~o~) + (0.005F~o~)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0365
_refine_ls_wR_factor_gt          0.0359
_refine_ls_wR_factor_ref         0.0359
_reflns_number_gt                3182
_reflns_number_total             3629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0654027si20060727_072834.cif
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C10 H16 Cl N O2 S '
_cod_database_code               4111146