Enantioselective Rhodium-Catalyzed [2 + 2 + 2] Cycloadditions of Terminal Alkynes and Alkenyl Isocyanates: Mechanistic Insights Lead to a Unified Model that Rationalizes Product Selectivity
Derek M. Dalton; Kevin M. Oberg; Robert T. Yu; Ernest E. Lee; Stéphane Perreault; Mark Emil Oinen; Melissa L. Pease; Guillaume Malik; Tomislav Rovis; Journal of the American Chemical Society 131 (2009) 15717–15728; doi:10.1021/ja905065j

data_4105229
_publ_section_title
;
 Enantioselective Rhodium-Catalyzed [2 + 2 + 2] Cycloadditions of Terminal
 Alkynes and Alkenyl Isocyanates: Mechanistic Insights Lead to a Unified
 Model that Rationalizes Product Selectivity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15717
_journal_page_last               15728
_journal_paper_doi               10.1021/ja905065j
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C34 H50 Cl N O2 P Rh'
_chemical_formula_weight         674.08
_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                77.003(3)
_cell_angle_beta                 76.360(2)
_cell_angle_gamma                64.354(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4105(5)
_cell_length_b                   10.8685(6)
_cell_length_c                   16.5368(10)
_cell_measurement_reflns_used    9703
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      33.29
_cell_measurement_theta_min      2.30
_cell_volume                     1622.99(16)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_molecular_graphics    'APEX2 (Bruker, 2009)'
_computing_publication_material  'APEX2 (Bruker, 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  '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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19235
_diffrn_reflns_theta_full        33.37
_diffrn_reflns_theta_max         33.37
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.8890
_exptl_absorpt_correction_T_min  0.6455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Trapazoidal
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         12140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0228P)^2^+1.6833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0792
_reflns_number_gt                10644
_reflns_number_total             12140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja905065j_si_002.cif
_cod_data_source_block           rovis41_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not determined' was changed to
'?' - the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1622.99(15)
_cod_database_code               4105229