Palladium-Catalyzed α-Arylation of Vinylogous Esters for the Synthesis of γ,γ-Disubstituted Cyclohexenones.
Johnson, Thomas; Pultar, Felix; Menke, Friedericke; Lautens, Mark; Organic letters 18 (2016) 6488–6491; doi:10.1021/acs.orglett.6b03394

data_1555989
_publ_section_title
;
 Palladium-Catalyzed \a-Arylation of Vinylogous Esters for the Synthesis
 of \g,\g-Disubstituted Cyclohexenones.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6488
_journal_page_last               6491
_journal_paper_doi               10.1021/acs.orglett.6b03394
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C18 H21 N O2'
_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_weight         283.36
_space_group_crystal_system      monoclinic
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_space_group_name_H-M_alt        'P 1 21/n 1'
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_cell_angle_alpha                90
_cell_angle_beta                 97.262(2)
_cell_angle_gamma                90
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_cell_length_a                   12.2561(4)
_cell_length_b                   15.5951(5)
_cell_length_c                   16.3454(6)
_cell_measurement_reflns_used    9735
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      67.09
_cell_measurement_theta_min      3.93
_cell_volume                     3099.12(18)
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_computing_data_collection       'APEX2 (Bruker, 2014)'
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_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
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_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_theta_full        67.194
_diffrn_reflns_theta_max         67.194
_diffrn_reflns_theta_min         3.933
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       Block
_exptl_crystal_F_000             1216
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_exptl_crystal_size_min          0.160
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_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         5510
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+1.4778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5195
_reflns_number_total             5510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03394_si_002.cif
_cod_data_source_block           d1672_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1555989
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.845
_shelx_estimated_absorpt_t_max   0.907
_shelx_res_checksum              92869
_shelx_hkl_checksum              11674