Re(I)-Catalyzed Hydropropargylation of Silyl Enol Ethers Utilizing Dynamic Interconversion of Vinylidene-Alkenylmetal Intermediates via 1,5-Hydride Transfer.
Iwasawa, Nobuharu; Watanabe, Shoya; Ario, Akane; Sogo, Hideyuki; Journal of the American Chemical Society 140 (2018) 7769–7772; doi:10.1021/jacs.8b02903

data_4132320
_publ_section_title
;
 Re(I)-Catalyzed Hydropropargylation of Silyl Enol Ethers Utilizing
 Dynamic Interconversion of Vinylidene-Alkenylmetal Intermediates via
 1,5-Hydride Transfer.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7769
_journal_page_last               7772
_journal_paper_doi               10.1021/jacs.8b02903
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C12 H12 O'
_chemical_formula_weight         172.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 104.888(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6225(6)
_cell_length_b                   5.2027(3)
_cell_length_c                   17.6456(10)
_cell_measurement_reflns_used    5913
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.0880
_cell_measurement_theta_min      1.9530
_cell_volume                     942.46(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       dtproprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11777
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         2.565
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       Prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.177
_refine_ls_abs_structure_details
;
 Flack x determined using 1103 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4264
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.135
_refine_ls_shift/su_mean         0.030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0815P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1526
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                3043
_reflns_number_total             4264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02903_si_002.cif
_cod_data_source_block           JJcrstal
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132320
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              43215
_shelx_hkl_checksum              96528