Copper(I) catalyzed regioselective asymmetric alkoxyamination of aryl enamide derivatives.
Nakanishi, Masafumi; Minard, Corinne; Retailleau, Pascal; Cariou, Kevin; Dodd, Robert H.; Organic letters 13 (2011) 5792–5795; doi:10.1021/ol202367d

data_1502534
_publ_section_title
;
 Copper(I) catalyzed regioselective asymmetric alkoxyamination of aryl
 enamide derivatives.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5792
_journal_page_last               5795
_journal_paper_doi               10.1021/ol202367d
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C28 H27 N3 O7 S2'
_chemical_formula_sum            'C28 H27 N3 O7 S2'
_chemical_formula_weight         581.65
_chemical_name_systematic
; 
N-(1-ethoxy-2-(4-nitrophenylsulfonamido)
-2-phenylethyl)-N-phenylbenzenesulfonamide 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.45(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.901(5)
_cell_length_b                   9.946(5)
_cell_length_c                   26.646(10)
_cell_measurement_reflns_used    5194
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      0.407
_cell_volume                     2841(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32908
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+1.2893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                3817
_reflns_number_total             5579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202367d_si_002.cif
_cod_data_source_block           mn1-14
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1502534