Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
Aurélien Alix; Claudia Lalli; Pascal Retailleau; Géraldine Masson; Journal of the American Chemical Society 134 (2012) 10389–10392; doi:10.1021/ja304095z

data_4118158
_publ_contact_author_address
;
Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email       @icsn.cnrs-gif.fr
_publ_contact_author_fax         +33169077247
_publ_contact_author_phone       +3316982
_publ_section_title
;
 Highly Enantioselective Electrophilic \a-Bromination of Enecarbamates:
 Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10389
_journal_page_last               10392
_journal_paper_doi               10.1021/ja304095z
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C15 H17 Br N2 O4'
_chemical_formula_weight         369.22
_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_date             10-05-10
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 152.431(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.7772(9)
_cell_length_b                   9.0850(2)
_cell_length_c                   13.8410(9)
_cell_measurement_temperature    193(2)
_cell_volume                     801.8(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6397
_diffrn_reflns_theta_full        68.17
_diffrn_reflns_theta_max         68.17
_diffrn_reflns_theta_min         6.60
_exptl_absorpt_coefficient_mu    3.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                2376
_reflns_number_total             2527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja304095z_si_002.cif
_cod_data_source_block           233
_cod_original_cell_volume        801.79(8)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4118158