Highly Chemoselective Rauhut-Currier Reaction between Maleimides and Enones and Dual Phosphine-Mediated One-Pot Synthesis of Bicyclic and Polycyclic Skeletons
Rong Zhou; Jianfang Wang; Jia Yu; Zhengjie He; Journal of Organic Chemistry 78 (2013) 10596–10604; doi:10.1021/jo401363u

data_4028692
_publ_section_title
;
 Highly Chemoselective Rauhut-Currier Reaction between Maleimides and
 Enones and Dual Phosphine-Mediated One-Pot Synthesis of Bicyclic and
 Polycyclic Skeletons
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10596
_journal_page_last               10604
_journal_paper_doi               10.1021/jo401363u
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C22 H18 Cl N O4'
_chemical_formula_weight         395.82
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.70(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.561(4)
_cell_length_b                   7.9588(16)
_cell_length_c                   13.637(3)
_cell_measurement_reflns_used    4714
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9584
_cell_measurement_theta_min      2.8102
_cell_volume                     1905.1(7)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18439
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.035(3)
_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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1634
_reflns_number_gt                2319
_reflns_number_total             4484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401363u_si_002.cif
_cod_data_source_block           r120723c1
_cod_database_code               4028692