Highly Regio- and Diastereoselective Anionic [3 + 2] Cycloaddition under Phase Transfer Catalytic Conditions
Vincent Gembus; Svetlana Postikova; Vincent Levacher; Jean-François Brière; Journal of Organic Chemistry 76 (2011) 4194–4199; doi:10.1021/jo2005268

data_4026324
_publ_contact_author_address
;CNRS UMR COBRA, Universit\'e et INSA de Rouen
FR INC3M 3038, IRCOF
rue Tesni\`ere
F-76821 Mont Saint Aignan cedex
;
_publ_contact_author_email       jean-francois.briere@insa-rouen.fr
_publ_contact_author_name        'Jean-Fran\,cois Bri\`ere'
_publ_section_title
;
 Highly Regio- and Diastereoselective Anionic [3 + 2] Cycloaddition under
 Phase Transfer Catalytic Conditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4194
_journal_page_last               4199
_journal_paper_doi               10.1021/jo2005268
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H24 Cl1 N1 O3'
_chemical_formula_sum            'C23 H24 Cl N O3'
_chemical_formula_weight         397.88
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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      2.3
_audit_creation_date             2011-02-08T17:19:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.6870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2634(8)
_cell_length_b                   9.4146(6)
_cell_length_c                   16.7765(10)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1984.4(2)
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.02
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15427
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0576P)^2^+0.4609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                3361
_reflns_number_total             4047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2005268_si_002.cif
_cod_data_source_block           vg1010bis
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026324