Memory of Chirality of Tertiary Aromatic Amides: A Simple and Efficient Method for the Enantioselective Synthesis of Quaternary α-Amino Acids
Mathieu Branca; Sébastien Pena; Régis Guillot; Didier Gori; Valérie Alezra; Cyrille Kouklovsky; Journal of the American Chemical Society 131 (2009) 10711–10718; doi:10.1021/ja9039604

data_4104773
_publ_contact_author_address
;Laboratoire de Chimie des Proc\'ed\'es et Substances Naturelles,
ICMMO, 
CNRS UMR 8182,
B\^at 410, 
Univ. Paris-Sud,
F-91405 Orsay. 
;
_publ_contact_author_email       valezra@icmo.u-psud.fr
_publ_contact_author_fax         '(00) 33 1 69 15 46 7'
_publ_contact_author_name        'Val\'erie Alezra'
_publ_contact_author_phone       '(00) 33 1 69 15 76 5'
_publ_section_title
;
 Memory of Chirality of Tertiary Aromatic Amides: A Simple and Efficient
 Method for the Enantioselective Synthesis of Quaternary \a-Amino Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10711
_journal_page_last               10718
_journal_paper_doi               10.1021/ja9039604
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N O3 S'
_chemical_formula_sum            'C20 H23 N O3 S'
_chemical_formula_weight         357.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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                 91.512(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7125(15)
_cell_length_b                   7.4605(9)
_cell_length_c                   11.5388(17)
_cell_measurement_reflns_used    4725
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.56
_cell_volume                     921.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9682
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.77
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4592
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0615P)^2^+0.0967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                4180
_reflns_number_total             4592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9039604_si_006.cif
_cod_data_source_block           810GuillotICMMO
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4104773