Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes: Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations.
Shintani, Ryo; Moriya, Kohei; Hayashi, Tamio; Organic letters 14 (2012) 2902–2905; doi:10.1021/ol301191u

data_1507751
_publ_section_title
;
 Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes:
 Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes
 and Mechanistic Considerations.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2902
_journal_page_last               2905
_journal_paper_doi               10.1021/ol301191u
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C15 H20 O3 Si '
_chemical_formula_sum            'C15 H20 O3 Si'
_chemical_formula_weight         276.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.70836(13)
_cell_length_b                   11.9909(2)
_cell_length_c                   17.7089(3)
_cell_measurement_reflns_used    6136
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.7
_cell_volume                     1424.49(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      93(1)
_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_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14813
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    1.474
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.744
_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    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1075 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2598
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.3455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                2379
_reflns_number_total             2598
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol301191u_si_004.cif
_cod_data_source_block           '_20218yuki'
_cod_original_cell_volume        1424.49(5)
_cod_original_formula_sum        'C15 H20 O3 Si '
_cod_database_code               1507751