Amplification of Anti-Diastereoselectivity via Curtin-Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers
Jason R. Zbieg; Emma L. McInturff; Joyce C. Leung; Michael J. Krische; Journal of the American Chemical Society 133 (2011) 1141–1144; doi:10.1021/ja1104156

data_4105554
_publ_section_title
;
 Amplification of Anti-Diastereoselectivity via Curtin-Hammett Effects in
 Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes:
 Diastereoselective Formation of All-Carbon Quaternary Centers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1141
_journal_page_last               1144
_journal_paper_doi               10.1021/ja1104156
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C20 H18 N2 O5'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.958(5)
_cell_angle_beta                 75.473(5)
_cell_angle_gamma                80.710(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3019(6)
_cell_length_b                   9.615(9)
_cell_length_c                   13.028(2)
_cell_measurement_reflns_used    5450
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.0
_cell_measurement_theta_min      6.0
_cell_volume                     854.0(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Rigaku R-Axis Spider with image plate'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7885
_diffrn_reflns_theta_full        66.56
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         6.52
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       needles
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0081(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0808P)^2^+0.3373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.2202
_reflns_number_gt                1487
_reflns_number_total             2924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1104156_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4105554