Z- and Enantioselective Ring-Opening/Cross-Metathesis with Enol Ethers Catalyzed by Stereogenic-at-Ru Carbenes: Reactivity, Selectivity, and Curtin-Hammett Kinetics
R. Kashif M. Khan; Robert V. O'Brien; Sebastian Torker; Bo Li; Amir H. Hoveyda; Journal of the American Chemical Society 134 (2012) 12774–12779; doi:10.1021/ja304827a

data_4118426
_publ_section_title
;
 Z- and Enantioselective Ring-Opening/Cross-Metathesis with Enol Ethers
 Catalyzed by Stereogenic-at-Ru Carbenes: Reactivity, Selectivity, and
 Curtin-Hammett Kinetics
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12774
_journal_page_last               12779
_journal_paper_doi               10.1021/ja304827a
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H17 Br O2'
_chemical_formula_sum            'C15 H17 Br O2'
_chemical_formula_weight         309.20
_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            8
_cell_length_a                   4.6190(2)
_cell_length_b                   18.6734(6)
_cell_length_c                   35.2274(10)
_cell_measurement_reflns_used    9289
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.69
_cell_measurement_theta_min      2.51
_cell_volume                     3038.45(19)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5243
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.50
_diffrn_reflns_theta_min         2.51
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    3.625
_exptl_absorpt_correction_T_max  0.9310
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_platon_squeeze_details
;
 Slovents are the mixture of dibutylehter and diethylether which are disordered
;
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(2)
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0412P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                4538
_reflns_number_total             5243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja304827a_si_001.cif
_cod_data_source_block           C15H17BrO2
_cod_database_code               4118426