Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton
Daisuke Uraguchi; Natsuko Kinoshita; Takashi Ooi; Journal of the American Chemical Society 132 (2010) 12240–12242; doi:10.1021/ja105945z

data_4103029
_publ_section_title
;
 Catalytic Asymmetric Protonation of \a-Amino Acid-Derived Ketene Disilyl
 Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12240
_journal_page_last               12242
_journal_paper_doi               10.1021/ja105945z
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C58 H45 N2 O4 P'
_chemical_formula_weight         864.93
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.528(5)
_cell_length_b                   12.447(2)
_cell_length_c                   13.383(2)
_cell_measurement_reflns_used    2202
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      20.96
_cell_measurement_theta_min      2.21
_cell_volume                     4585.6(13)
_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      153(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0830
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34830
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9890
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         11404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0835
_refine_ls_shift/su_max          0.165
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+1.7005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1557
_reflns_number_gt                8696
_reflns_number_total             11404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja105945z_si_003.cif
_cod_data_source_block           1b
_cod_original_cell_volume        4585.6(14)
_cod_database_code               4103029