Three Component Coupling of α-Iminoesters via Umpolung Addition of Organometals: Synthesis of α,α-Disubstituted α-Amino Acids
Joshua S. Dickstein; Michael W. Fennie; Amber L. Norman; Betty J. Paulose; Marisa C. Kozlowski; Journal of the American Chemical Society 130 (2008) 15794–15795; doi:10.1021/ja8073006

data_4108756
_publ_section_title
;
 Three Component Coupling of \a-Iminoesters via Umpolung Addition of
 Organometals: Synthesis of \a,\a-Disubstituted \a-Amino Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15794
_journal_page_last               15795
_journal_paper_doi               10.1021/ja8073006
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C32 H34 N2 O5 S'
_chemical_formula_weight         558.67
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.616(8)
_cell_angle_beta                 94.121(9)
_cell_angle_gamma                103.653(8)
_cell_formula_units_Z            2
_cell_length_a                   11.9729(16)
_cell_length_b                   12.259(2)
_cell_length_c                   12.508(2)
_cell_measurement_temperature    143(1)
_cell_volume                     1576.6(4)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11760
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
   Shape function based on spherical harmonics.
   Highest even and odd order for spherical harmonics:  4  and  1
   Laue group:  -1
   Friedel opposites are equivalent.
;
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0632
_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^)+(0.0706P)^2^+2.2154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1743
_reflns_number_gt                4288
_reflns_number_total             5500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8073006_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1576.7(4)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4108756