Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization.
Peng, Yu; Xiao, Jian; Xu, Xiao-Bo; Duan, Shu-Ming; Ren, Li; Shao, Yong-Liang; Wang, Ya-Wen; Organic letters 18 (2016) 5170–5173; doi:10.1021/acs.orglett.6b02665

data_1555847
_publ_section_title
;
 Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a
 Nickel-Promoted Tandem Reductive Cyclization.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5170
_journal_page_last               5173
_journal_paper_doi               10.1021/acs.orglett.6b02665
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C13 H14 O2'
_chemical_formula_weight         202.24
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.317(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8052(4)
_cell_length_b                   10.2396(8)
_cell_length_c                   15.2160(9)
_cell_measurement_reflns_used    1172
_cell_measurement_temperature    291.76(10)
_cell_measurement_theta_max      28.5255
_cell_measurement_theta_min      3.0353
_cell_volume                     1043.15(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.76(10)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3359
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0387P)^2^+0.3265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                1458
_reflns_number_total             1958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02665_si_005.cif
_cod_data_source_block           xuxiaobo0915
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1555847