Chiral Brønsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction
Hua Liu; Guillaume Dagousset; Géraldine Masson; Pascal Retailleau; Jieping Zhu; Journal of the American Chemical Society 131 (2009) 4598–4599; doi:10.1021/ja900806q

data_4104145
_publ_contact_author_address
;
ICSN-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
;
 Chiral Br\/onsted Acid-Catalyzed Enantioselective Three-Component Povarov
 Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4598
_journal_page_last               4599
_journal_paper_doi               10.1021/ja900806q
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H21 Cl N2 O2, 0.72(C2 H6 O)'
_chemical_formula_sum            'C24.44 H25.32 Cl N2 O2.72'
_chemical_formula_weight         426.04
_chemical_name_systematic
; 
 benzyl-6-chloro-2-phenyl-1,2,3,4-tetrahydroquinolin-4-ylcarbamate 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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             07-01-09
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.962(3)
_cell_length_b                   13.451(5)
_cell_length_c                   34.045(10)
_cell_measurement_reflns_used    1343
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.82
_cell_measurement_theta_min      1.00
_cell_volume                     2272.3(17)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            2295
_diffrn_reflns_theta_full        20.85
_diffrn_reflns_theta_max         20.85
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             898.9
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.129
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(18)
_refine_ls_extinction_coef       0.035(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0656
_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^)+(0.1231P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.1749
_reflns_number_gt                1834
_reflns_number_total             2295
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja900806q_si_001.cif
_cod_data_source_block           sqz_gd161
_cod_database_code               4104145