Copper-Mediated Oxidative Transformation of N-Allyl Enamine Carboxylates toward Synthesis of Azaheterocycles.
Toh, Kah Kah; Biswas, Anup; Wang, Yi-Feng; Tan, Yun Yun; Chiba, Shunsuke; Journal of the American Chemical Society 136 (2014) 6011–6020; doi:10.1021/ja500382c

data_4121683
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_section_title
;
 Copper-Mediated Oxidative Transformation of N-Allyl Enamine Carboxylates
 toward Synthesis of Azaheterocycles.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6011
_journal_page_last               6020
_journal_paper_doi               10.1021/ja500382c
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C21 H23 N O4 S'
_chemical_formula_weight         385.46
_chemical_name_common            leung758s
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 92.078(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0086(12)
_cell_length_b                   8.0000(9)
_cell_length_c                   26.351(4)
_cell_measurement_reflns_used    1590
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      25.4663
_cell_measurement_theta_min      2.3642
_cell_volume                     1897.8(4)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_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      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14101
_diffrn_reflns_theta_full        29.28
_diffrn_reflns_theta_max         29.28
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.770
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0823P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                3196
_reflns_number_total             5076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja500382c_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 4121683.cif.'
_cod_database_code               4121683
_shelx_res_checksum              46356
_shelx_hkl_checksum              23487