Catalytic Asymmetric Total Synthesis of (+)- and (−)-Paeoveitol via a Hetero-Diels–Alder Reaction
Li, Tian-Ze; Geng, Chang-An; Yin, Xiu-Juan; Yang, Tong-Hua; Chen, Xing-Long; Huang, Xiao-Yan; Ma, Yun-Bao; Zhang, Xue-Mei; Chen, Ji-Jun; Organic Letters  (2017) –; doi:10.1021/acs.orglett.6b03801

data_1545164
_publ_section_title
;
 Catalytic Asymmetric Total Synthesis of (+)- and (&#x2212;)-Paeoveitol
 via a Hetero-Diels--Alder Reaction
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.6b03801
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H20 O5'
_chemical_formula_sum            'C19 H20 O5'
_chemical_formula_weight         328.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.114(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9838(7)
_cell_length_b                   9.0762(3)
_cell_length_c                   9.3006(3)
_cell_measurement_reflns_used    4404
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.96
_cell_measurement_theta_min      4.69
_cell_volume                     1590.16(9)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.962
_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  0.0570
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5157
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.784
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.512
_diffrn_reflns_theta_min         4.695
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7532
_exptl_transmission_factor_min   0.4086
_refine_diff_density_max         1.338
_refine_diff_density_min         -1.863
_refine_diff_density_rms         0.233
_refine_ls_abs_structure_details
;
 Flack x determined using 696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.582
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.625
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.1469
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3267
_refine_ls_wR_factor_ref         0.3289
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_full    0.597
_reflns_Friedel_fraction_max     0.579
_reflns_number_gt                2224
_reflns_number_total             2339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03801_si_002.cif
_cod_data_source_block           cu_jltz01_0m
_cod_database_code               1545164
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.640
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              71080
_shelx_hkl_checksum              70286