Direct β-Functionalization of Cyclic Ketones with Aryl Ketones via the Merger of Photoredox and Organocatalysis
Filip R. Petronijević; Manuel Nappi; David W. C. MacMillan; Journal of the American Chemical Society 135 (2013) 18323–18326; doi:10.1021/ja410478a

data_4121295
_publ_section_title
;
 Direct \b-Functionalization of Cyclic Ketones with Aryl Ketones via the
 Merger of Photoredox and Organocatalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18323
_journal_page_last               18326
_journal_paper_doi               10.1021/ja410478a
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.38
_chemical_name_common            152-2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_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
_cell_angle_alpha                90
_cell_angle_beta                 99.129(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.318(3)
_cell_length_b                   16.115(6)
_cell_length_c                   10.684(4)
_cell_measurement_reflns_used    8899
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      64.5839
_cell_measurement_theta_min      2.7422
_cell_volume                     1584.0(10)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2012.6.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8974
_diffrn_reflns_theta_full        64.72
_diffrn_reflns_theta_max         64.72
_diffrn_reflns_theta_min         5.01
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       'Irregular prism'
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.184
_refine_ls_extinction_coef       0.0047(6)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.7329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                2480
_reflns_number_total             2517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja410478a_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        1584.0(9)
_cod_database_code               4121295