Organocatalyzed Asymmetric Vinylogous Addition of Oxazole-2(3H)-thiones to α,β-Unsaturated Ketones: An Additive-Free Approach for Diversification of Heterocyclic Scaffold.
Silva, Sandrina; Matsuo, Bianca T.; da Silva, Rodrigo C.; Pozzi, Lucas V.; Correa, Arlene G.; Rollin, Patrick; Zukerman-Schpector, Julio; Ferreira, Marco A. B.; Paixão, Márcio W; The Journal of organic chemistry 83 (2018) 1701–1716; doi:10.1021/acs.joc.7b02236

data_4033462
_publ_section_title
;
 Organocatalyzed Asymmetric Vinylogous Addition of Oxazole-2(3H)-thiones
 to \a,\b-Unsaturated Ketones: An Additive-Free Approach for
 Diversification of Heterocyclic Scaffold.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1701
_journal_page_last               1716
_journal_paper_doi               10.1021/acs.joc.7b02236
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H14 F N O2 S'
_chemical_formula_sum            'C14 H14 F N O2 S'
_chemical_formula_weight         279.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90.926(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0004(7)
_cell_length_b                   16.3880(10)
_cell_length_c                   9.7835(8)
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.80
_cell_measurement_theta_min      2.42
_cell_volume                     1442.86(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10752
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_min         2.082
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2012-1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       irregular
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.402
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(34)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5456
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.3372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                4174
_reflns_number_total             5456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02236_si_003.cif
_cod_data_source_block           JZS-4
_cod_depositor_comments          'Adding full bibliography for 4033462.cif.'
_cod_database_code               4033462
_shelx_estimated_absorpt_t_min   0.894
_shelx_estimated_absorpt_t_max   0.952
_shelxl_version_number           2014/6
_shelx_res_checksum              61201
_shelx_hkl_checksum              14128