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_4121294
_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 H21 O2'
_chemical_formula_weight         293.37
_chemical_name_common            161-1-B
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 114.30(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.45(2)
_cell_length_b                   9.900(17)
_cell_length_c                   12.67(2)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    273.(2)
_cell_measurement_theta_max      35.7349
_cell_measurement_theta_min      3.5355
_cell_volume                     1538(4)
_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      273.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38210
_diffrn_reflns_theta_full        35.85
_diffrn_reflns_theta_max         35.85
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.280
_refine_diff_density_max         1.012
_refine_diff_density_min         -0.281
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         7098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          4.683
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0982P)^2^+0.5255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1633
_reflns_number_gt                6270
_reflns_number_total             7098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja410478a_si_001.cif
_cod_data_source_block           I
_cod_original_cell_volume        1538.(5)
_cod_database_code               4121294