Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation
Emma L. McInturff; Eiji Yamaguchi; Michael J. Krische; Journal of the American Chemical Society 134 (2012) 20628–20631; doi:10.1021/ja311208a

data_4119060
_publ_section_title
;
 Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in
 Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene
 Hydrohydroxyalkylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20628
_journal_page_last               20631
_journal_paper_doi               10.1021/ja311208a
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety
; 
C38 H28 P2 O4, C31 H28 P O6 1-, C2 H3 O2 1-, Ru 2+, 
 C O, C4 H8 O
;
_chemical_formula_sum            'C76 H67 O14 P3 Ru'
_chemical_formula_weight         1398.28
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_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                 115.146(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.919(4)
_cell_length_b                   11.0585(18)
_cell_length_c                   26.886(4)
_cell_measurement_reflns_used    33971
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     6976(2)
_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      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury 2 CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_av_sigmaI/netI    0.1743
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            33971
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       laths
_exptl_crystal_F_000             2896
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     837
_refine_ls_number_reflns         15604
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1790
_reflns_number_gt                9539
_reflns_number_total             15604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311208a_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        6976.1(19)
_cod_database_code               4119060