Rhodium-Catalyzed Enantioselective 1,6-Addition of Arylboronic Acids to Enynamides: Asymmetric Synthesis of Axially Chiral Allenylsilanes
Takahiro Nishimura; Hiroki Makino; Makoto Nagaosa; Tamio Hayashi; Journal of the American Chemical Society 132 (2010) 12865–12867; doi:10.1021/ja1066509

data_4103074
_publ_section_title
;
 Rhodium-Catalyzed Enantioselective 1,6-Addition of Arylboronic Acids to
 Enynamides: Asymmetric Synthesis of Axially Chiral Allenylsilanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12865
_journal_page_last               12867
_journal_paper_doi               10.1021/ja1066509
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C56 H52 F4 N O Rh Si, 0.32(C H2 Cl2)'
_chemical_formula_sum            'C56.33 H52.65 Cl0.65 F4 N O Rh Si'
_chemical_formula_weight         989.60
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.810(2)
_cell_length_b                   14.161(3)
_cell_length_c                   28.699(5)
_cell_measurement_reflns_used    42781
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     4799.7(15)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_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         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            45271
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2047
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     697
_refine_ls_number_reflns         10929
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+5.2977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                10023
_reflns_number_total             10929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1066509_si_002.cif
_cod_data_source_block           100420yuki
_cod_original_cell_volume        4799.5(17)
_cod_database_code               4103074