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_4119008
_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 unk
_chemical_formula_moiety         'C14 H17 N O3'
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.29
_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             2012-09-25
_audit_creation_method           'by CrystalStructure 4.0'
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.248(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.0718(17)
_cell_length_b                   9.922(3)
_cell_length_c                   19.048(5)
_cell_measurement_reflns_used    5189
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.99
_cell_volume                     1330.9(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    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5639
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       needle
_exptl_crystal_F_000             528.00
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5512
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0846P)^2^+0.7505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1988
_reflns_number_gt                4828
_reflns_number_total             5512
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja310203c_si_003.cif
_cod_data_source_block           comp10
_cod_database_code               4119008