Rhodium-Catalyzed Enantioselective Vinylogous Addition of Enol Ethers to Vinyldiazoacetates
Austin G. Smith; Huw M. L. Davies; Journal of the American Chemical Society 134 (2012) 18241–18244; doi:10.1021/ja3092399

data_4118873
_publ_section_title
;
 Rhodium-Catalyzed Enantioselective Vinylogous Addition of Enol Ethers to
 Vinyldiazoacetates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18241
_journal_page_last               18244
_journal_paper_doi               10.1021/ja3092399
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H38 O3 Si2'
_chemical_formula_sum            'C22 H38 O3 Si2'
_chemical_formula_weight         406.70
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-03-09
_audit_creation_method
; 
  Olex2 1.2-alpha 
  (compiled Mar  9 2012 11:03:06, GUI svn.r4114) 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.0651(2)
_cell_length_b                   20.1439(4)
_cell_length_c                   27.5076(5)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      67.96
_cell_measurement_theta_min      3.21
_cell_volume                     5023.07(17)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2011.2-4 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_publication_material
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.2
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX2 detector'
_diffrn_measurement_method       '\f and \w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            36602
_diffrn_reflns_theta_full        68.91
_diffrn_reflns_theta_max         68.91
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'sealed tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.4
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.410
_exptl_absorpt_correction_T_max  0.9652
_exptl_absorpt_correction_T_min  0.7265
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
R(int) was 0.0964 before and 0.0467 after correction. 
The Ratio of minimum to maximum transmission is 0.7527. 
The \l/2 correction factor is Not present. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_description       needle
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.842
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         9081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.1730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                8811
_reflns_number_total             9081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3092399_si_002.cif
_cod_data_source_block           agsiii155b
_cod_database_code               4118873