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_7112475
_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 R
_chemical_formula_sum            'C21 H23 O5 P'
_chemical_formula_weight         386.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.647(3)
_cell_length_b                   9.403(4)
_cell_length_c                   24.219(9)
_cell_measurement_reflns_used    4467
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.17
_cell_volume                     1969.2(13)
_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 8.366[pixels/mm]
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13602
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         2.324
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       prizm
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.427
_refine_diff_density_min         -1.436
_refine_diff_density_rms         0.161
_refine_ls_abs_structure_details
; 
 Flack x determined using 1448 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0790
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2186
_refine_ls_wR_factor_ref         0.2896
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3795
_reflns_number_total             4824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc49338e.txt
_cod_data_source_block           3Y06mit
_cod_original_cell_volume        1969.0(13)
_cod_database_code               7112475
_shelxl_version_number           2013-3
_shelx_res_checksum              63515
_shelx_hkl_checksum              40748