Asymmetric Allylation of Furfural Derivatives: Synergistic Effect of Chiral Ligand and Organocatalyst on Stereochemical Control
Su, Yong-Liang; Han, Zhi-Yong; Li, Yu-Hui; Gong, Liu-Zhu; ACS Catalysis 7 (2017) 7917–; doi:10.1021/acscatal.7b02667

data_4514250
_publ_section_title
;
 Asymmetric Allylation of Furfural Derivatives: Synergistic Effect of
 Chiral Ligand and Organocatalyst on Stereochemical Control
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7917
_journal_paper_doi               10.1021/acscatal.7b02667
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H20 O4'
_chemical_formula_sum            'C20 H20 O4'
_chemical_formula_weight         324.36
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6577(2)
_cell_length_b                   8.9036(2)
_cell_length_c                   32.5408(8)
_cell_measurement_reflns_used    7781
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      69.947
_cell_measurement_theta_min      4.967
_cell_volume                     1639.21(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.68
_diffrn_measured_fraction_theta_full 0.988
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            10681
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.022
_diffrn_reflns_theta_min         5.437
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1543 before and 0.0843 after correction. The Ratio of minimum to maximum transmission is 0.6385. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 1107 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.2887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2875
_reflns_number_total             3061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b02667_si_002.cif
_cod_data_source_block           cu_d8v17097_0m
_cod_depositor_comments          'Adding full bibliography for 4514250.cif.'
_cod_database_code               4514250
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.897
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_res_checksum              66808
_shelx_hkl_checksum              30445
_olex2_submission_special_instructions 'No special instructions were received'