Ligand-controlled E/Z selectivity and enantioselectivity in palladium-catalyzed allylation of benzofuranones with 1,2-disubstituted allylic carbonates
Kohsuke Ohmatsu; Mitsunori Ito; Takashi Ooi; Chem.Commun. 50 (2014) 4554–; doi:10.1039/C3CC49338E

data_7112476
_publ_section_title
;
 Ligand-controlled E/Z selectivity and enantioselectivity in
 palladium-catalyzed allylation of benzofuranones with 1,2-disubstituted
 allylic carbonates
;
_journal_name_full               Chem.Commun.
_journal_page_first              4554
_journal_paper_doi               10.1039/C3CC49338E
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration S
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.710(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6395(10)
_cell_length_b                   15.610(2)
_cell_length_c                   7.8147(12)
_cell_measurement_reflns_used    3125
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.61
_cell_volume                     809.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 80366[pixels/mm]
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5814
_diffrn_reflns_point_group_measured_fraction_full 0.812
_diffrn_reflns_point_group_measured_fraction_max 0.791
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.270
_diffrn_reflns_theta_min         2.608
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       prizm
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 916 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0839P)^2^+0.1219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.534
_reflns_Friedel_fraction_full    0.609
_reflns_Friedel_fraction_max     0.571
_reflns_number_gt                3031
_reflns_number_total             3186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc49338e.txt
_cod_data_source_block           3Y12mit
_cod_database_code               7112476
_shelxl_version_number           2013-3
_shelx_res_checksum              11417
_shelx_hkl_checksum              69724