Highly Diastereo- and Enantioselective Cu-Catalyzed [3 + 3] Cycloaddition of Propargyl Esters with Cyclic Enamines toward Chiral Bicyclo[n.3.1] Frameworks
Cheng Zhang; Xin-Hu Hu; Ya-Hui Wang; Zhuo Zheng; Jie Xu; Xiang-Ping Hu; Journal of the American Chemical Society 134 (2012) 9585–9588; doi:10.1021/ja303129s

data_4118054
_publ_section_title
;
 Highly Diastereo- and Enantioselective Cu-Catalyzed [3 + 3] Cycloaddition
 of Propargyl Esters with Cyclic Enamines toward Chiral Bicyclo[n.3.1]
 Frameworks
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9585
_journal_page_last               9588
_journal_paper_doi               10.1021/ja303129s
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration R
_chemical_formula_sum            'C31 H29 Cl3 Cu Fe N2 P'
_chemical_formula_weight         686.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 111.428(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.4605(6)
_cell_length_b                   10.9335(6)
_cell_length_c                   13.1568(7)
_cell_measurement_reflns_used    5188
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      2.50
_cell_volume                     1534.64(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9139
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    1.502
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.031(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4994
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.0257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                4647
_reflns_number_total             4994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303129s_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        1534.64(14)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4118054