Copper-catalyzed enantioselective propargylic etherification of propargylic esters with alcohols.
Nakajima, Kazunari; Shibata, Masashi; Nishibayashi, Yoshiaki; Journal of the American Chemical Society 137 (2015) 2472–2475; doi:10.1021/jacs.5b00004

data_4129275
_publ_section_title
;
 Copper-catalyzed enantioselective propargylic etherification of
 propargylic esters with alcohols.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2472
_journal_page_last               2475
_journal_paper_doi               10.1021/jacs.5b00004
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C48 H39 Cu2 F6 N6 O10.50 S2'
_chemical_formula_sum            'C48 H39 Cu2 F6 N6 O10.5 S2'
_chemical_formula_weight         1173.07
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   15.7607(8)
_cell_length_b                   16.9627(9)
_cell_length_c                   18.2945(10)
_cell_measurement_reflns_used    17305
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.06
_cell_volume                     4890.9(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            39548
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  0.829
_exptl_absorpt_correction_T_min  0.341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2388.00
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         2.250
_refine_diff_density_min         -1.620
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  4619 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     690
_refine_ls_number_reflns         10633
_refine_ls_R_factor_gt           0.1089
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[7.9200\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                7941
_reflns_number_total             10633
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja5b00004_si_002.cif
_cod_data_source_block           20140210
_cod_original_cell_volume        4890.9(5)
_cod_original_formula_sum        'C48 H39 Cu2 F6 N6 O10.50 S2'
_cod_database_code               4129275