Synthesis of Silyloxy Dienes by Silylene Transfer to Divinyl Ketones: Application to the Asymmetric Synthesis of Substituted Cyclohexanes
Christian C. Ventocilla; K. A. Woerpel; Journal of Organic Chemistry 77 (2012) 3277–3283; doi:10.1021/jo202650k

data_4027105
_publ_section_title
;
 Synthesis of Silyloxy Dienes by Silylene Transfer to Divinyl Ketones:
 Application to the Asymmetric Synthesis of Substituted Cyclohexanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3277
_journal_page_last               3283
_journal_paper_doi               10.1021/jo202650k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C28 H42 O5 Si'
_chemical_formula_weight         486.71
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                115.8638(14)
_cell_angle_beta                 100.4816(15)
_cell_angle_gamma                103.0340(15)
_cell_formula_units_Z            2
_cell_length_a                   11.2829(10)
_cell_length_b                   12.0507(11)
_cell_length_c                   12.1302(11)
_cell_measurement_reflns_used    962
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.83
_cell_volume                     1370.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      163(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15210
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_description       hexagon
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0481P)^2^+0.3811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                5412
_reflns_number_total             6619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202650k_si_002.cif
_cod_data_source_block           kaw102
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4027105