Cationic Rhodium(I) Complex-Catalyzed [3 + 2] and [2 + 1] Cycloadditions of Propargyl Esters with Electron-Deficient Alkynes and Alkenes
Yu Shibata; Keiichi Noguchi; Ken Tanaka; Journal of the American Chemical Society 132 (2010) 7896–7898; doi:10.1021/ja102418h

data_4102522
_publ_contact_author_address
;
Department of Applied Chemistry
Graduate School of Engineering
Tokyo University of Agriculture and Technology
Koganei
Tokyo 184-8588
Japan
;
_publ_contact_author_email       tanaka-k@cc.tuat.ac.jp
_publ_contact_author_fax         +81-42-388-7037
_publ_contact_author_name        'Dr Ken Tanaka'
_publ_contact_author_phone       +81-42-388-7037
_publ_section_title
;
 Cationic Rhodium(I) Complex-Catalyzed [3 + 2] and [2 + 1] Cycloadditions
 of Propargyl Esters with Electron-Deficient Alkynes and Alkenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7896
_journal_page_last               7898
_journal_paper_doi               10.1021/ja102418h
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C14 H21 N O5'
_chemical_formula_sum            'C14 H21 N O5'
_chemical_formula_weight         283.32
_chemical_name_systematic
;
 1-(1-Acetoxy-2-methylpropenyl)-2-dimethylcarbamoylcyclopropanecarboxylic
 acid methyl ester
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-01-29
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.6993(4)
_cell_length_b                   6.8584(2)
_cell_length_c                   28.0209(8)
_cell_measurement_reflns_used    29466
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      70.9
_cell_measurement_theta_min      3.2
_cell_volume                     3017.07(15)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.2043
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2824
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1776
_refine_ls_R_factor_gt           0.1264
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0130P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2780
_refine_ls_wR_factor_ref         0.3200
_reflns_number_gt                970
_reflns_number_total             2824
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja102418h_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        3017.05(15)
_cod_database_code               4102522