Construction of Contiguous Tetrasubstituted Chiral Carbon Stereocenters via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Esters with Ketones
Tatsuhiko Yoshino; Hiroyuki Morimoto; Gang Lu; Shigeki Matsunaga; Masakatsu Shibasaki; Journal of the American Chemical Society 131 (2009) 17082–17083; doi:10.1021/ja908571w

data_4105423
_publ_section_title
;
 Construction of Contiguous Tetrasubstituted Chiral Carbon Stereocenters
 via Direct Catalytic Asymmetric Aldol Reaction of \a-Isothiocyanato
 Esters with Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17082
_journal_page_last               17083
_journal_paper_doi               10.1021/ja908571w
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C13 H15 N O3 S '
_chemical_formula_sum            'C13 H15 N O3 S'
_chemical_formula_weight         265.33
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.73624(16)
_cell_length_b                   11.8091(2)
_cell_length_c                   12.2419(2)
_cell_measurement_reflns_used    13557
_cell_measurement_temperature    98.1
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      3.6
_cell_volume                     1262.96(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14235
_diffrn_reflns_theta_full        68.15
_diffrn_reflns_theta_max         68.15
_exptl_absorpt_coefficient_mu    2.292
_exptl_absorpt_correction_T_max  0.765
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             560.00
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.65
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  964 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2314
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0007Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                2132
_reflns_number_total             2314
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja908571w_si_002.cif
_cod_data_source_block           '_090608tythioisocyanato'
_cod_original_cell_volume        1262.97(4)
_cod_original_formula_sum        'C13 H15 N O3 S '
_cod_database_code               4105423