A New Family of Cinchona-Derived Amino Phosphine Precatalysts: Application to the Highly Enantio- and Diastereoselective Silver-Catalyzed Isocyanoacetate Aldol Reaction
Filippo Sladojevich; Andrea Trabocchi; Antonio Guarna; Darren J. Dixon; Journal of the American Chemical Society 133 (2011) 1710–1713; doi:10.1021/ja110534g

data_4105637
_publ_contact_author             'Darren J. Dixon'
_publ_contact_author_email       darren.dixon@chem.ox.ac.uk
_publ_section_title
;
 A New Family of Cinchona-Derived Amino Phosphine Precatalysts:
 Application to the Highly Enantio- and Diastereoselective
 Silver-Catalyzed Isocyanoacetate Aldol Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1710
_journal_page_last               1713
_journal_paper_doi               10.1021/ja110534g
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_sum            'C17 H14.67 F N O3.33'
_chemical_formula_weight         305.30
_space_group_IT_number           146
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   25.205(8)
_cell_length_b                   25.205(8)
_cell_length_c                   5.987(3)
_cell_measurement_reflns_used    686
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.48
_cell_measurement_theta_min      3.23
_cell_volume                     3294(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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1288
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       needle
_exptl_crystal_F_000             1434
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1288
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.1247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                1082
_reflns_number_total             1288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja110534g_si_002.cif
_cod_data_source_block           z:\s3049\work\s3049twa
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4105637