Iron-Catalyzed Dioxygen-Driven C-C Bond Formation: Oxidative Dearomatization of 2-Naphthols with Construction of a Chiral Quaternary Stereocenter
Takuya Oguma; Tsutomu Katsuki; Journal of the American Chemical Society 134 (2012) 20017–20020; doi:10.1021/ja310203c

data_4119007
_publ_contact_author_email       katsuscc@chem.kyushu-univ.jp
_publ_contact_author_name        'Tsutomu Katsuki'
_publ_section_title
;
 Iron-Catalyzed Dioxygen-Driven C-C Bond Formation: Oxidative
 Dearomatization of 2-Naphthols with Construction of a Chiral Quaternary
 Stereocenter
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20017
_journal_page_last               20020
_journal_paper_doi               10.1021/ja310203c
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H13 Cl2 N O3'
_chemical_formula_sum            'C18 H13 Cl2 N O3'
_chemical_formula_weight         362.21
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-09-25
_audit_creation_method           'by CrystalStructure 4.0'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.7451(13)
_cell_length_b                   14.825(3)
_cell_length_c                   16.546(4)
_cell_measurement_reflns_used    3654
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.11
_cell_measurement_theta_min      3.01
_cell_volume                     1654.5(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Schneider, et al., 2002)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3766
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       platelet
_exptl_crystal_F_000             744.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.220
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1593 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.06(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0828
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0362P)^2^+2.5200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1627
_reflns_number_gt                2423
_reflns_number_total             3766
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja310203c_si_002.cif
_cod_data_source_block           comp6
_cod_database_code               4119007