Palladium catalyzed asymmetric allylation of 3-OBoc-oxindoles: an efficient synthesis of 3-allyl-3-hydroxyoxindoles.
Jayakumar, Samydurai; Kumarswamyreddy, Nandarapu; Prakash, Muthuraj; Kesavan, Venkitasamy; Organic letters 17 (2015) 1066–1069; doi:10.1021/acs.orglett.5b00034

data_1554767
_publ_section_title
;
 Palladium catalyzed asymmetric allylation of 3-OBoc-oxindoles: an
 efficient synthesis of 3-allyl-3-hydroxyoxindoles.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1066
_journal_page_last               1069
_journal_paper_doi               10.1021/acs.orglett.5b00034
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H24 Cl N O3'
_chemical_formula_sum            'C31 H24 Cl N O3'
_chemical_formula_weight         493.96
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.161(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0810(4)
_cell_length_b                   19.4060(12)
_cell_length_c                   9.4910(6)
_cell_measurement_reflns_used    4863
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.84
_cell_measurement_theta_min      2.16
_cell_volume                     1290.99(14)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20014
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.749
_diffrn_reflns_theta_min         2.099
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9599
_exptl_absorpt_correction_T_min  0.9421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_coef       0.019(4)
_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   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4917
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0638P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2980
_reflns_number_total             4917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00034_si_002.cif
_cod_data_source_block           KUMARSWAMY
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554767
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.956
_shelx_res_checksum              802
_shelx_hkl_checksum              85566