Rhodium-Phosphoramidite Catalyzed Alkene Hydroacylation: Mechanism and Octaketide Natural Product Synthesis
Max von Delius; Christine M. Le; Vy M. Dong; Journal of the American Chemical Society 134 (2012) 15022–15032; doi:10.1021/ja305593y

data_4118593
_publ_section_title
;
 Rhodium-Phosphoramidite Catalyzed Alkene Hydroacylation: Mechanism and
 Octaketide Natural Product Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15022
_journal_page_last               15032
_journal_paper_doi               10.1021/ja305593y
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H26 O6'
_chemical_formula_sum            'C18 H26 O6'
_chemical_formula_weight         338.39
_space_group_IT_number           1
_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                108.517(2)
_cell_angle_beta                 101.863(2)
_cell_angle_gamma                115.104(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0136(5)
_cell_length_b                   10.1157(5)
_cell_length_c                   10.9568(5)
_cell_measurement_reflns_used    9229
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      4.60
_cell_volume                     874.95(8)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_source         'Bruker Microsource'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.021
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32251
_diffrn_reflns_theta_full        67.39
_diffrn_reflns_theta_max         67.39
_diffrn_reflns_theta_min         4.64
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6063
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0616P)^2^+0.4889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                5827
_reflns_number_total             6063
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja305593y_si_002.cif
_cod_data_source_block           cu_d12103_0m
_cod_original_cell_volume        874.95(7)
_cod_database_code               4118593