Organocatalytic direct asymmetric aldol reactions of 3-isothiocyanato oxindoles to ketones: stereocontrolled synthesis of spirooxindoles bearing highly congested contiguous tetrasubstituted stereocenters.
Chen, Wen-Bing; Wu, Zhi-Jun; Hu, Jing; Cun, Lin-Feng; Zhang, Xiao-Mei; Yuan, Wei-Cheng; Organic letters 13 (2011) 2472–2475; doi:10.1021/ol200724q

data_1502158
_publ_section_title
;
 Organocatalytic direct asymmetric aldol reactions of 3-isothiocyanato
 oxindoles to ketones: stereocontrolled synthesis of spirooxindoles
 bearing highly congested contiguous tetrasubstituted stereocenters.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2472
_journal_page_last               2475
_journal_paper_doi               10.1021/ol200724q
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H24 N2 O3 S2'
_chemical_formula_weight         452.57
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.803(4)
_cell_angle_beta                 76.579(4)
_cell_angle_gamma                89.515(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8593(5)
_cell_length_b                   11.3699(6)
_cell_length_c                   11.6474(6)
_cell_measurement_reflns_used    4774
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.3078
_cell_measurement_theta_min      4.2274
_cell_volume                     1171.33(11)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7543
_diffrn_reflns_theta_full        69.43
_diffrn_reflns_theta_max         69.43
_diffrn_reflns_theta_min         4.23
_exptl_absorpt_coefficient_mu    2.283
_exptl_absorpt_correction_T_max  0.5286
_exptl_absorpt_correction_T_min  0.4620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         5134
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0814P)^2^+0.2513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                4861
_reflns_number_total             5134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200724q_si_002.cif
_cod_data_source_block           ywc-1
_cod_original_cell_volume        1171.33(10)
_cod_database_code               1502158