Experimental Evidence for the All-Up Reactive Conformation of Chiral Rhodium(II) Carboxylate Catalysts: Enantioselective Synthesis of cis-Cyclopropane α-Amino Acids
Vincent N. G. Lindsay; Wei Lin; André B. Charette; Journal of the American Chemical Society 131 (2009) 16383–16385; doi:10.1021/ja9044955

data_4105351
_publ_contact_author_address
;
      Universit\'e de Montr\'eal
      D\'epartement de Chimie
      C.P. 6128, Succ. Centre-ville
      Montr\'eal, Qu\'ebec
      Canada, H3C 3J7
;
_publ_contact_author_email       andre.charette@umontreal.ca
_publ_contact_author_fax         '+1 514 343 5900'
_publ_contact_author_name        'Dr Andr\'e B. Charette'
_publ_contact_author_phone       '+1 514 343 6283'
_publ_section_title
;
 Experimental Evidence for the All-Up Reactive Conformation of Chiral
 Rhodium(II) Carboxylate Catalysts: Enantioselective Synthesis of
 cis-Cyclopropane \a-Amino Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16383
_journal_page_last               16385
_journal_paper_doi               10.1021/ja9044955
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C60 H64 N4 O20 Rh2'
_chemical_formula_sum            'C60 H64 N4 O20 Rh2'
_chemical_formula_weight         1366.97
_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                 92.792(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0549(19)
_cell_length_b                   21.667(3)
_cell_length_c                   18.052(2)
_cell_measurement_reflns_used    14691
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.5
_cell_measurement_theta_min      2.2
_cell_volume                     6272.1(13)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 v2.4-0 (Bruker AXS, 2007)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         'X-ray sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.07
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            94491
_diffrn_reflns_theta_full        23.82
_diffrn_reflns_theta_max         23.82
_diffrn_reflns_theta_min         1.13
_diffrn_standards_decay_%        5.4
_diffrn_standards_interval_time  900
_diffrn_standards_number         1802
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Twinabs (Sheldrick, 1996)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             2808
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 'Flack H D (1983), 12456 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1454
_refine_ls_number_reflns         22391
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0926P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                19101
_reflns_number_total             22391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9044955_si_005.cif
_cod_data_source_block           cha177
_cod_original_cell_volume        6272.3(13)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4105351