Enantioselective [4 + 2] Cycloaddition of CyclicN-Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones
Liu, Yong; Kang, Tai-Ran; Liu, Quan-Zhong; Chen, Lian-Mei; Wang, Ya-Chuan; Liu, Jie; Xie, Yong-Mei; Yang, Jin-Liang; He, Long; Organic Letters 15 (2013) 6090–; doi:10.1021/ol402977w

data_1513153
_publ_section_title
;
 Enantioselective [4 + 2] Cycloaddition of CyclicN-Sulfimines and Acyclic
 Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted
 Piperidin-4-ones
;
_journal_issue                   23
_journal_name_full               'Organic Letters'
_journal_page_first              6090
_journal_paper_doi               10.1021/ol402977w
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H21 N O4 S'
_chemical_formula_weight         335.41
_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                 107.491(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2550(8)
_cell_length_b                   8.8201(7)
_cell_length_c                   10.2868(8)
_cell_measurement_reflns_used    1711
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.1300
_cell_measurement_theta_min      3.0994
_cell_volume                     800.89(12)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4034
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.9548
_exptl_absorpt_correction_T_min  0.9124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_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     208
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0520P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                2546
_reflns_number_total             2775
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402977w_si_002.cif
_cod_data_source_block           ly130518
_cod_original_cell_volume        800.89(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1513153