Copper-Catalyzed Desymmetrization of Prochiral 4,4-Disubstituted Cyclopentenes via a Site-Selective Allylic Oxidation Reaction: A Concise Total Synthesis of Untenone A
Gui, Qingwen; Wang, JuanJuan; Ng, Sean; Dancevic, Anja; Wright, Timothy B.; Evans, P. Andrew; Chemical Communications  (2019) –; doi:10.1039/C9CC01743G

data_7123764
_publ_section_title
;
 Copper-Catalyzed Desymmetrization of Prochiral 4,4-Disubstituted
 Cyclopentenes via a Site-Selective Allylic Oxidation Reaction: A Concise
 Total Synthesis of Untenone A
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01743G
_journal_year                    2019
_chemical_formula_moiety         'C14 H14 O5'
_chemical_formula_sum            'C14 H14 O5'
_chemical_formula_weight         262.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1mgkbz
_audit_creation_method           'manual editing of SHELXL-2014/7 template'
_audit_update_record
;
2019-01-16 deposited with the CCDC.    2019-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.3100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5934(2)
_cell_length_b                   6.2414(2)
_cell_length_c                   26.6906(7)
_cell_measurement_reflns_used    6229
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.43
_cell_measurement_theta_min      2.388
_cell_volume                     1261.38(6)
_computing_cell_refinement
' Saint V8.35A and SADABS v2014/5 (Apex3, v2015.9-0; Bruker AXS)'
_computing_data_collection
' APEX2 software package v2013.10-0 (Bruker AXS)'
_computing_data_reduction
' Saint V8.35A and SADABS V2014/5 (Apex3, v2015.9-0; Bruker AXS'
_computing_molecular_graphics    ' XP (SHELXTL-NT v6.14, Bruker AXS)'
_computing_structure_refinement  ' SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ' SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images,\f and \w scans'
_diffrn_radiation_monochromator  'horizontal mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            12425
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         1.530
_diffrn_source                   'Bruker AXS K780, fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2012/1 (Apex2, Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0575P)^2^+0.3865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3015
_reflns_number_total             3582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01743g2.cif
_cod_data_source_block           pgqw01_2016_0m
_cod_database_code               7123764
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              47741