Enantioselective Bromoaminocyclization of Allyl N-Tosylcarbamates Catalyzed by a Chiral Phosphine-Sc(OTf)3 Complex
Deshun Huang; Xiaoqin Liu; Lijun Li; Yudong Cai; Weigang Liu; Yian Shi; Journal of the American Chemical Society 135 (2013) 8101–8104; doi:10.1021/ja4010877

data_4119830
_publ_section_title
;
 Enantioselective Bromoaminocyclization of Allyl N-Tosylcarbamates
 Catalyzed by a Chiral Phosphine-Sc(OTf)3 Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8101
_journal_page_last               8104
_journal_paper_doi               10.1021/ja4010877
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H16 N4 O4 S'
_chemical_formula_sum            'C13 H16 N4 O4 S'
_chemical_formula_weight         324.36
_chemical_name_systematic
; 
 ? 
;
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.184(3)
_cell_length_b                   7.9032(16)
_cell_length_c                   27.865(6)
_cell_measurement_reflns_used    194
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      0.73
_cell_volume                     3123.6(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            30537
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         0.73
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_correction_T_min  0.9446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.140
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(16)
_refine_ls_extinction_coef       0.0104(10)
_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   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     802
_refine_ls_number_reflns         10963
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.1101
_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^)+(0.0819P)^2^+17.4540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2677
_refine_ls_wR_factor_ref         0.2849
_reflns_number_gt                8941
_reflns_number_total             10963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4010877_si_005.cif
_cod_data_source_block           sa2385
_cod_original_cell_volume        3123.8(11)
_cod_database_code               4119830