A highly enantioselective and regioselective organocatalytic direct Mannich reaction of methyl alkyl ketones with cyclic imines benzo[e][1,2,3]oxathiazine 2,2-dioxides.
Wang, You-Qing; Cui, Xiao-Yu; Ren, Yuan-Yuan; Zhang, Yongna; Organic & biomolecular chemistry 12 (2014) 9101–9104; doi:10.1039/c4ob01902d

data_7154109
_publ_section_title
;
 A highly enantioselective and regioselective organocatalytic direct
 Mannich reaction of methyl alkyl ketones with cyclic imines
 benzo[e][1,2,3]oxathiazine 2,2-dioxides.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9101
_journal_page_last               9104
_journal_paper_doi               10.1039/c4ob01902d
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C10 H10 Cl N O4 S'
_chemical_formula_weight         275.70
_chemical_name_systematic
(S)-1-(6-chloro-2,2-dioxido-3,4-dihydrobenzo[e][1,2,3]oxathiazin-4-yl)propan-2-one
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.3279(9)
_cell_length_b                   14.1730(17)
_cell_length_c                   22.626(3)
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.804
_cell_measurement_theta_min      2.301
_cell_volume                     2349.9(5)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2(Bruker, 2005)'
_computing_data_reduction        'SAINT(Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL(Bruker, 2005)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Smart APEX II 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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14969
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle-like
_exptl_crystal_F_000             1136
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0423P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                3716
_reflns_number_total             5800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01902d2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7154109.cif.'
_cod_original_sg_symbol_Hall     p_2ac_2ab
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7154109