Enantioselective Intramolecular Oxidative Aminocarbonylation of Alkenylureas Catalyzed by Palladium-Spiro Bis(isoxazoline) Complexes
Tetsuya Tsujihara; Toshio Shinohara; Kazuhiro Takenaka; Shinobu Takizawa; Kiyotaka Onitsuka; Minoru Hatanaka; Hiroaki Sasai; Journal of Organic Chemistry 74 (2009) 9274–9279; doi:10.1021/jo901778a

data_4025091
_publ_contact_author_address
;
    The Institute of Scientific and Industrial Research
    Osaka University
    8-1 Mihogaoka, Ibaraki
    Osaka 567-0047, Japan
;
_publ_contact_author_email       sasai@sanken.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6879-8469
_publ_contact_author_name        'Hiroaki SASAI'
_publ_contact_author_phone       +81-6-6879-8465
_publ_section_title
;
Enantioselective Intramolecular Oxidative Aminocarbonylation of
Alkenylureas Catalyzed by Palladium-Spiro Bis(isoxazoline) Complexes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9274
_journal_page_last               9279
_journal_paper_doi               10.1021/jo901778a
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C16 H20 N2 O4 S '
_chemical_formula_sum            'C16 H20 N2 O4 S'
_chemical_formula_weight         336.40
_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'
_audit_creation_date             2007-09-11
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.100(3)
_cell_length_b                   8.189(3)
_cell_length_c                   24.650(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      17.0
_cell_measurement_theta_min      15.1
_cell_volume                     1635.0(10)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR2002
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            5758
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             712.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.36
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2040 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.737
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4782
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0010Fo^2^ + 3.0000\s(Fo^2^) + 0.5000]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0686
_reflns_number_gt                4571
_reflns_number_total             4783
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo901778a_si_002.cif
_cod_data_source_block           '_o-tol_Urea_pro_c'
_cod_original_formula_sum        'C16 H20 N2 O4 S '
_cod_database_code               4025091