Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Brønsted base.
Kondoh, Azusa; Tran, Hoa Thi Quynh; Kimura, Kyoko; Terada, Masahiro; Chemical communications (Cambridge, England) 52 (2016) 5726–5729; doi:10.1039/c6cc01690a

data_7124610
_publ_section_title
;
 Enantioselective intramolecular cyclization of alkynyl esters catalyzed
 by a chiral Br\/onsted base.
;
_journal_issue                   33
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5726
_journal_page_last               5729
_journal_paper_doi               10.1039/c6cc01690a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 Br O2'
_chemical_formula_sum            'C17 H15 Br O2'
_chemical_formula_weight         331.19
_chemical_name_common            C17H15BrO2
_chemical_name_systematic
(Z)-(3-(4-Bromobenzylidene)-2-methyl-2,3-dihydrobenzofuran-2-yl)methanol
_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
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-10-16 deposited with the CCDC.
2016-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.991(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9605(6)
_cell_length_b                   32.909(3)
_cell_length_c                   7.1915(7)
_cell_measurement_reflns_used    9667
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      66.6743
_cell_measurement_theta_min      4.0299
_cell_volume                     1409.8(2)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker SMART APEXII ULTRA'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 goniometer with CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9636
_diffrn_reflns_theta_full        66.72
_diffrn_reflns_theta_max         66.72
_diffrn_reflns_theta_min         6.16
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Bruker Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    3.957
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'G. M. Sheldrick, (2012) SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.423
_refine_ls_abs_structure_details
;
Flack x determined using 2251 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.037(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4591
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0225
_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^)+(0.0235P)^2^+0.6089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0575
_reflns_number_gt                4587
_reflns_number_total             4591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc01690a2.cif
_cod_data_source_block           I
_cod_database_code               7124610
_shelx_res_checksum              50574
_shelx_hkl_checksum              64039