Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N-Heterobicyclic Enones
Megan H. Shaw; Ekaterina Y. Melikhova; Daniel P. Kloer; William G. Whittingham; John F. Bower; Journal of the American Chemical Society 135 (2013) 4992–4995; doi:10.1021/ja401936c

data_4119552
_publ_section_title
;
 Directing Group Enhanced Carbonylative Ring Expansions of
 Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent
 Synthesis of N-Heterobicyclic Enones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4992
_journal_page_last               4995
_journal_paper_doi               10.1021/ja401936c
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C11 H14 N O3'
_chemical_formula_sum            'C11 H14 N O3'
_chemical_formula_weight         208.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.972(5)
_cell_angle_beta                 87.261(4)
_cell_angle_gamma                71.917(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0198(14)
_cell_length_b                   8.3657(14)
_cell_length_c                   8.8594(15)
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.90
_cell_measurement_theta_min      5.40
_cell_volume                     522.19(16)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Microstar CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21295
_diffrn_reflns_theta_full        66.30
_diffrn_reflns_theta_max         66.30
_diffrn_reflns_theta_min         5.40
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.6131
_exptl_absorpt_correction_T_min  0.4216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1800
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0805P)^2^+0.2516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1411
_reflns_number_gt                1722
_reflns_number_total             1800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja401936c_si_003.cif
_cod_data_source_block           compound12b
_cod_original_cell_volume        522.19(15)
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4119552