NHC-Catalyzed Enantioselective Dearomatizing Hydroacylation of Benzofurans and Benzothiophenes for the Synthesis of Spirocycles
Janssen-Müller, Daniel; Fleige, Mirco; Schlüns, Danny; Wollenburg, Marco; Daniliuc, Constantin G.; Neugebauer, Johannes; Glorius, Frank; ACS Catalysis 6 (2016) 5735–; doi:10.1021/acscatal.6b01852

data_4513928
_publ_section_title
;
 NHC-Catalyzed Enantioselective Dearomatizing Hydroacylation of
 Benzofurans and Benzothiophenes for the Synthesis of Spirocycles
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              5735
_journal_paper_doi               10.1021/acscatal.6b01852
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H14 O2'
_chemical_formula_weight         250.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6908(4)
_cell_length_b                   10.3574(4)
_cell_length_c                   13.9701(6)
_cell_measurement_reflns_used    4322
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.4641
_cell_measurement_theta_min      5.3165
_cell_volume                     1257.51(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL--2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13195
_diffrn_reflns_theta_full        68.46
_diffrn_reflns_theta_max         68.46
_diffrn_reflns_theta_min         5.32
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.167
_refine_ls_abs_structure_details
;
Flack x determined using 837 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.2568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                2135
_reflns_number_total             2284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01852_si_002.cif
_cod_data_source_block           glo7754
_cod_depositor_comments          'Adding full bibliography for 4513928.cif.'
_cod_database_code               4513928
_shelx_res_checksum              87000
_shelx_hkl_checksum              32079