Catalytic cascade aldol-cyclization of tertiary ketone enolates for enantioselective synthesis of keto-esters with a C-F quaternary stereogenic center.
Sha, Wanxing; Zhang, Lijun; Zhang, Wenzhong; Mei, Haibo; Soloshonok, Vadim A.; Han, Jianlin; Pan, Yi; Organic & biomolecular chemistry 14 (2016) 7295–7303; doi:10.1039/c6ob01152g

data_7155194
_publ_section_title
;
 Catalytic cascade aldol-cyclization of tertiary ketone enolates for
 enantioselective synthesis of keto-esters with a C-F quaternary
 stereogenic center.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7295
_journal_page_last               7303
_journal_paper_doi               10.1039/c6ob01152g
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H12 Cl F O3'
_chemical_formula_weight         330.73
_space_group_IT_number           19
_symmetry_cell_setting           Orthorhombic'
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-25 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.958(3)
_cell_length_b                   9.449(3)
_cell_length_c                   19.866(6)
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.33
_cell_measurement_theta_min      2.39
_cell_volume                     1493.8(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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8451
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.9412
_exptl_absorpt_correction_T_min  0.9285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                1741
_reflns_number_total             2638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob01152g2.cif
_cod_data_source_block           11
_cod_depositor_comments          'Adding full bibliography for 7155194.cif.'
_cod_original_cell_volume        1493.9(8)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7155194