Lewis Acid Catalyzed Cyclization of Glycals/2-Deoxy-d-ribose with Arylamines: Additional Findings on Product Structure and Reaction Diastereoselectivity
Chengtang Du; Fulong Li; Xuefeng Zhang; Wenxiang Hu; Qizheng Yao; Ao Zhang; Journal of Organic Chemistry 76 (2011) 8833–8839; doi:10.1021/jo2015483

data_4026699
_publ_section_title
;
 Lewis Acid Catalyzed Cyclization of Glycals/2-Deoxy-d-ribose with
 Arylamines: Additional Findings on Product Structure and Reaction
 Diastereoselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8833
_journal_page_last               8839
_journal_paper_doi               10.1021/jo2015483
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_space_group_IT_number           152
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31 2"'
_symmetry_space_group_name_H-M   'P 31 2 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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   5.9830(4)
_cell_length_b                   5.9830(4)
_cell_length_c                   46.449(4)
_cell_measurement_reflns_used    5080
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.388
_cell_measurement_theta_min      5.262
_cell_volume                     1439.94(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            7801
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34116
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.169
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       0.056(8)
_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   1.309
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.309
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+0.3001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                1864
_reflns_number_total             1896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2015483_si_003.cif
_cod_data_source_block           cd21118
_cod_original_cell_volume        1439.94(19)
_cod_database_code               4026699