Enantioselective Synthesis of Axially Chiral Anilides through Rhodium-Catalyzed [2+2+2] Cycloaddition of 1,6-Diynes with Trimethylsilylynamides
Ken Tanaka; Kenzo Takeishi; Keiichi Noguchi; Journal of the American Chemical Society 128 (2006) 4586–4587; doi:10.1021/ja060348f

data_4110546
_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
;
 Enantioselective Synthesis of Axially Chiral Anilides through
 Rhodium-Catalyzed [2+2+2] Cycloaddition of 1,6-Diynes with
 Trimethylsilylynamides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4586
_journal_page_last               4587
_journal_paper_doi               10.1021/ja060348f
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H38 N2 O3 S Si'
_chemical_formula_sum            'C34 H38 N2 O3 S Si'
_chemical_formula_weight         582.81
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-01-10
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.942(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.7037(11)
_cell_length_b                   10.2735(4)
_cell_length_c                   19.8389(7)
_cell_measurement_reflns_used    55511
_cell_measurement_temperature    223
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.3
_cell_volume                     6344.2(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics
'ORTEP-3 for Windows Ver. 1.076 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     1.5418
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            60595
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       needle
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 5036 Friedel pairs'
_refine_ls_abs_structure_Flack   0.028(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     751
_refine_ls_number_reflns         11183
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+1.8297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                9656
_reflns_number_total             11183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja060348fsi20060117_071019.cif
_cod_data_source_block           I
_cod_database_code               4110546