Cu(OAc)2/TFA-promoted formal [3 + 3] cycloaddition/oxidation of enamines and enones for synthesis of multisubstituted aromatic amines.
Li, Liang; Zhao, Mi-Na; Ren, Zhi-Hui; Li, Jian-Li; Guan, Zheng-Hui; Organic letters 14 (2012) 3506–3509; doi:10.1021/ol3014733

data_1507887
_publ_section_title
;
 Cu(OAc)2/TFA-promoted formal [3 + 3] cycloaddition/oxidation of enamines
 and enones for synthesis of multisubstituted aromatic amines.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3506
_journal_page_last               3509
_journal_paper_doi               10.1021/ol3014733
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C21 H25 N2 O4'
_chemical_formula_weight         369.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.321(4)
_cell_length_b                   14.075(5)
_cell_length_c                   23.143(8)
_cell_measurement_reflns_used    1503
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.40
_cell_measurement_theta_min      2.37
_cell_volume                     4013(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19142
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+0.5874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1583
_reflns_number_gt                2093
_reflns_number_total             3584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3014733_si_004.cif
_cod_data_source_block           xb5297_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1507885--1507887.cif.
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1507887