Asymmetric Synthesis of Bicyclic Amidines via Rhodium-Catalyzed [2+2+2] Cycloaddition of Carbodiimides
Robert T. Yu; Tomislav Rovis; Journal of the American Chemical Society 130 (2008) 3262–3263; doi:10.1021/ja710065h

data_4107556
_publ_section_title
;
 Asymmetric Synthesis of Bicyclic Amidines via Rhodium-Catalyzed [2+2+2]
 Cycloaddition of Carbodiimides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3262
_journal_page_last               3263
_journal_paper_doi               10.1021/ja710065h
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H21 Br N2 O'
_chemical_formula_weight         397.31
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Bruker SHELXT'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.4508(13)
_cell_length_b                   14.332(3)
_cell_length_c                   38.051(8)
_cell_measurement_reflns_used    903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.49
_cell_measurement_theta_min      3.50
_cell_volume                     3517.9(13)
_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 SHELXT'
_computing_structure_solution    'Bruker SHELXT'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex2 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  0.1359
_diffrn_reflns_av_sigmaI/netI    0.2263
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            22084
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    2.348
_exptl_absorpt_correction_T_max  0.9161
_exptl_absorpt_correction_T_min  0.5729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Shedlrick, 1997'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       plates
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.016(19)
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         10257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          NaN
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                4317
_reflns_number_total             10257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja710065h-file001.cif
_cod_data_source_block           rovis29_0m
_cod_original_cell_volume        3518.0(13)
_cod_database_code               4107556