A Cooperative Participation of the Amido Group in the Organocatalytic Construction of All-Carbon Quaternary Stereocenters by Michael Addition with β-Ketoamides
Sanchez Duque, Maria del Mar; Baslé, Olivier; Isambert, Nicolas; Gaudel-Siri, Anouk; Génisson, Yves; Plaquevent, Jean-Christophe; Rodriguez, Jean; Constantieux, Thierry; Organic Letters 13 (2011) 3296–3299; doi:10.1021/ol200924e

data_1502207
_publ_section_title
;
 A Cooperative Participation of the Amido Group in the Organocatalytic
 Construction of All-Carbon Quaternary Stereocenters by Michael Addition
 with \b-Ketoamides
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   13
_journal_name_full               'Organic Letters'
_journal_page_first              3296
_journal_page_last               3299
_journal_paper_doi               10.1021/ol200924e
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H18 N2 O5'
_chemical_formula_sum            'C16 H18 N2 O5'
_chemical_formula_weight         318.32
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-09-01T15:54:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.509
_cell_length_b                   13.97
_cell_length_c                   10.942
_cell_measurement_reflns_used    14929
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.69
_cell_measurement_theta_min      1.99
_cell_measurement_wavelength     0.71073
_cell_volume                     1565.231
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.078
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14929
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.26
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6907
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.08
_refine_ls_shift/su_max          0.176
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1079P)^2^+1.2994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2363
_reflns_number_gt                4781
_reflns_number_total             6907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200924e_si_002.cif
_cod_data_source_block           tc1
_cod_original_cell_volume        1565.2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1502207