Diastereoselective conjugate addition of organocuprates to chiral N-enoyl oxazolidinethiones.
Sabala, Rocío; Hernández-García, Luis; Ortiz, Aurelio; Romero, Moisés; Olivo, Horacio F.; Organic letters 12 (2010) 4268–4270; doi:10.1021/ol101687e

data_1503185
_publ_section_title
;
 Diastereoselective conjugate addition of organocuprates to chiral N-enoyl
 oxazolidinethiones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4268
_journal_page_last               4270
_journal_paper_doi               10.1021/ol101687e
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H25 N O2 S'
_chemical_formula_sum            'C22 H25 N O2 S'
_chemical_formula_weight         367.49
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-11-08
_audit_creation_method           SHELXTL-Plus
_cell_angle_alpha                90.00
_cell_angle_beta                 96.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.437(2)
_cell_length_b                   16.067(6)
_cell_length_c                   11.335(4)
_cell_measurement_pressure       101(2)
_cell_measurement_reflns_used    94
_cell_measurement_temperature    298(1)
_cell_measurement_theta_max      11.66
_cell_measurement_theta_min      4.60
_cell_volume                     983.4(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'MERCURY CSD 2.0 (Macrae et al., 2006)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_pressure         101(2)
_diffrn_ambient_temperature      298(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7484
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.81
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_type              FN4
_diffrn_source_voltage           50
_diffrn_standards_decay_%        14
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9646
_exptl_absorpt_correction_T_min  0.2854
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;

Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166

;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1668 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.570
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.570
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.05P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                2939
_reflns_number_total             3482
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol101687e_si_005.cif
_cod_data_source_block           ao12
_cod_original_cell_volume        983.4(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1503185
_exptl_absorpt_factor_mur        0.036