Combining Ru-Catalyzed C-H Functionalization with Pd-Catalyzed Asymmetric Allylic Alkylation: Synthesis of 3-Allyl-3-aryl Oxindole Derivatives from Aryl α-Diazoamides.
Yamamoto, Kosuke; Qureshi, Zafar; Tsoung, Jennifer; Pisella, Guillaume; Lautens, Mark; Organic letters 18 (2016) 4954–4957; doi:10.1021/acs.orglett.6b02423

data_1544143
_publ_section_title
;
 Combining Ru-Catalyzed C-H Functionalization with Pd-Catalyzed Asymmetric
 Allylic Alkylation: Synthesis of 3-Allyl-3-aryl Oxindole Derivatives from
 Aryl \a-Diazoamides.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4954
_journal_page_last               4957
_journal_paper_doi               10.1021/acs.orglett.6b02423
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H21 N O'
_chemical_formula_sum            'C24 H21 N O'
_chemical_formula_weight         339.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 90.128(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9816(4)
_cell_length_b                   29.4224(15)
_cell_length_c                   13.9309(7)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      65.88
_cell_measurement_theta_min      3.17
_cell_volume                     3681.4(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
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_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0544
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
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_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            78021
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.374
_diffrn_reflns_theta_max         67.374
_diffrn_reflns_theta_min         3.004
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6009
_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       Block
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_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
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_refine_diff_density_min         -0.313
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; 
 Flack x determined using 5491 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         12912
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0311P)^2^+2.3281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                12237
_reflns_number_total             12912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02423_si_002.cif
_cod_data_source_block           d1687_a
_cod_depositor_comments          'Adding full bibliography for 1544143.cif.'
_cod_database_code               1544143
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.903
_shelx_estimated_absorpt_t_max   0.934
_shelx_res_checksum              10191
_shelx_hkl_checksum              66036