Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction.
Wu, Xiang; Lin, Hua-Chen; Li, Ming-Li; Li, Lu-Lu; Han, Zhi-Yong; Gong, Liu-Zhu; Journal of the American Chemical Society 137 (2015) 13476–13479; doi:10.1021/jacs.5b08734

data_4129606
_publ_section_title
;
 Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral
 Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation
 Reaction.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13476
_journal_page_last               13479
_journal_paper_doi               10.1021/jacs.5b08734
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H21 F3 O4'
_chemical_formula_sum            'C22 H21 F3 O4'
_chemical_formula_weight         406.39
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.688(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3002(10)
_cell_length_b                   5.7332(6)
_cell_length_c                   37.635(4)
_cell_measurement_reflns_used    2936
_cell_measurement_temperature    130
_cell_measurement_theta_max      66.862
_cell_measurement_theta_min      2.364
_cell_volume                     1993.0(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            14860
_diffrn_reflns_point_group_measured_fraction_full 0.762
_diffrn_reflns_point_group_measured_fraction_max 0.740
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.212
_diffrn_reflns_theta_min         1.182
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1318 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.7623.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0995P)^2^+1.8583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.1982
_reflns_Friedel_coverage         0.396
_reflns_Friedel_fraction_full    0.492
_reflns_Friedel_fraction_max     0.471
_reflns_number_gt                4982
_reflns_number_total             5587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08734_si_002.cif
_cod_data_source_block           cu_dm15393_0m
_cod_database_code               4129606
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.834
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C31(H31), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C30(H30), C39(H39), C40(H40), C42(H42), C43(H43)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C)
;
_shelx_res_checksum              85608
_shelx_hkl_checksum              65445
_olex2_submission_special_instructions 'No special instructions were received'