Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)<sub>2</sub>-Catalyzed Reactions of Ynamides with <i>t</i>-Butyl Carbamates/Carbonates.
Han, Pan; Mao, Zhuo-Ya; Li, Ming; Si, Chang-Mei; Wei, Bang-Guo; Lin, Guo-Qiang; The Journal of organic chemistry 85 (2020) 4740–4752; doi:10.1021/acs.joc.9b03512

data_4038081
_publ_section_title
;
 Synthesis of Amide Enol Carbamates and Carbonates through
 Cu(OTf)<sub>2</sub>-Catalyzed Reactions of Ynamides with <i>t</i>-Butyl
 Carbamates/Carbonates.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4740
_journal_page_last               4752
_journal_paper_doi               10.1021/acs.joc.9b03512
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H28 N2 O6 S'
_chemical_formula_weight         508.57
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.7680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0988(2)
_cell_length_b                   9.9019(2)
_cell_length_c                   13.2271(3)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.700
_cell_measurement_theta_min      4.776
_cell_volume                     1310.54(5)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18622
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.388
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
; 
 Flack x determined using 1952 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.050(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5128
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.0764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4607
_reflns_number_total             5128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03512_si_003.cif
_cod_data_source_block           mo_d8v18987_0m
_cod_depositor_comments
'Adding full bibliography for 4038081--4038082.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038081
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              33976
_shelx_hkl_checksum              1858