Organocatalytic Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids and Derivatives
Silvia Cabrera; Efraim Reyes; José Alemán; Andrea Milelli; Sara Kobbelgaard; Karl Anker Jørgensen; Journal of the American Chemical Society 130 (2008) 12031–12037; doi:10.1021/ja804567h

data_4108311
_publ_contact_author             'Overgaard, Jacob'
_publ_contact_author_email       jacobo@chem.au.dk
_publ_section_title
;
 Organocatalytic Asymmetric Synthesis of \a,\a-Disubstituted \a-Amino
 Acids and Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12031
_journal_page_last               12037
_journal_paper_doi               10.1021/ja804567h
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C33 H42 N5 O6 S2, C26 H35 N3 O5 S, C4 H8 O2'
_chemical_formula_sum            'C63 H85 N8 O13 S3'
_chemical_formula_weight         1258.57
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-02-10T20:41:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.194(2)
_cell_length_b                   17.001(3)
_cell_length_c                   31.552(6)
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.5
_cell_measurement_theta_min      2.4
_cell_measurement_wavelength     0.71073
_cell_volume                     6541(2)
_computing_cell_refinement       'Saint+ v7.46A (Bruker-Nonius, 2007)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2007)'
_computing_data_reduction        'Saint+ v7.46A (Bruker-Nonius, 2007)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1729
_diffrn_reflns_av_unetI/netI     0.1255
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36160
_diffrn_reflns_theta_full        18.85
_diffrn_reflns_theta_max         18.85
_diffrn_reflns_theta_min         3.4
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       prism
_exptl_crystal_F_000             2684
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.117
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1631
_reflns_number_gt                3542
_reflns_number_total             5111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja804567h_si_002.cif
_cod_data_source_block           p212121
_cod_original_cell_volume        6541(3)
_cod_database_code               4108311