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_4103028
_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            'C84 H57 Cl9 N4 O5 P2'
_chemical_formula_weight         1583.33
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 95.025(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.478(3)
_cell_length_b                   14.753(3)
_cell_length_c                   16.184(3)
_cell_measurement_reflns_used    6476
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.23
_cell_volume                     3681.4(12)
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28185
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_correction_T_min  0.8784
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     947
_refine_ls_number_reflns         18050
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0867P)^2^+0.9764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                15483
_reflns_number_total             18050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja105945z_si_002.cif
_cod_data_source_block           1a
_cod_original_cell_volume        3681.3(11)
_cod_database_code               4103028