Combined Photoredox and Lewis Acid Catalyzed α-Hydroxyalkylation of Cyclic Ethers with Aromatic Ketones.
Reckenthäler, Melissa; Neudörfl, Jörg-M; Zorlu, Elif; Griesbeck, Axel G.; The Journal of organic chemistry 81 (2016) 7211–7216; doi:10.1021/acs.joc.6b01085

data_4036965
_publ_section_title
;
 Combined Photoredox and Lewis Acid Catalyzed \a-Hydroxyalkylation of
 Cyclic Ethers with Aromatic Ketones.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7211
_journal_page_last               7216
_journal_paper_doi               10.1021/acs.joc.6b01085
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C12 H16 O3'
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
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_cell_angle_beta                 100.1720(10)
_cell_angle_gamma                90
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_cell_length_b                   8.1671(3)
_cell_length_c                   11.3491(4)
_cell_measurement_reflns_used    14120
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.739
_cell_measurement_theta_min      6.715
_cell_volume                     1111.86(7)
_computing_cell_refinement       'Bruker APEX 2'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker APEX 2'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
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_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
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_diffrn_reflns_limit_k_min       -9
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_diffrn_reflns_limit_l_min       -14
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_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.739
_diffrn_reflns_theta_min         6.715
_diffrn_source                   microfocus
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_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
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_refine_diff_density_min         -0.290
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_refine_ls_extinction_coef       0.028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.4530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2075
_reflns_number_total             2202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01085_si_001.cif
_cod_data_source_block           mr327
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036965
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.813
_shelx_estimated_absorpt_t_max   0.931
_shelx_res_checksum              46708
_shelx_hkl_checksum              55605