4-Alkenyl-5H-1,2,3-oxathiazole 2,2-dioxides in catalytic and enantioselective [4 + 2] cycloaddition through iminium activation. Straightforward access to the trans-decaline framework and to densely functionalized cyclohexanes
Riaño, Iker; Uria, Uxue; Carrillo, Luisa; Reyes, Efraim; Vicario, Jose L.; Organic Chemistry Frontiers 2 (2015) 206–; doi:10.1039/C4QO00316K

data_1553060
_publ_section_title
;
 4-Alkenyl-5H-1,2,3-oxathiazole 2,2-dioxides in catalytic and
 enantioselective [4 + 2] cycloaddition through iminium activation.
 Straightforward access to the trans-decaline framework and to densely
 functionalized cyclohexanes
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              206
_journal_paper_doi               10.1039/C4QO00316K
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H17 N1 O4 S1'
_chemical_formula_sum            'C12 H17 N O4 S'
_chemical_formula_weight         271.33
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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             2014-11-18T11:23:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-11-18 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.77410(10)
_cell_length_b                   9.74090(10)
_cell_length_c                   14.53650(10)
_cell_measurement_reflns_used    18185
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.898
_cell_measurement_theta_min      4.523
_cell_measurement_wavelength     1.54184
_cell_volume                     1242.40(2)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   21.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7631 -125.0000   30.0000 72

  2 omega   14.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   19.0000    0.0000 107

  3 omega  -47.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000  -60.0000 33

  4 omega   36.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000    0.0000 26

  5 omega   35.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -90.0000 39

  6 omega   40.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -30.0000 34

  7 omega   24.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -120.0000 67

  8 omega   40.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   60.0000 29

  9 omega   43.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -60.0000 25

 10 omega   35.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   30.0000 34

 11 omega   79.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  150.0000 48

 12 omega   28.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -60.0000 80

 13 omega   20.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7631 -125.0000 -180.0000 69

 14 omega   21.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   38.0000   90.0000 93

 15 omega  -52.00   -9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000  -90.0000 43

 16 omega   41.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 28

 17 omega   30.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   90.0000 25

 18 omega   37.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   60.0000 79

 19 omega   85.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609    0.0000 -120.0000 73

 20 omega   89.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000  -90.0000 26

 21 omega  130.00  156.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000  -90.0000 26

 22 omega   31.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000    0.0000 38

 23 omega   40.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -120.0000 81

 24 omega   22.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609    0.0000 -120.0000 55

 25 omega   73.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000   60.0000 44

 26 omega -119.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -77.0000  -90.0000 112

 27 omega -119.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -77.0000    0.0000 112

 28 omega    7.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   77.0000 -180.0000 112

 29 omega  -33.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7631  -57.0000  -60.0000 103

 30 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   57.0000  120.0000 104

 31 omega -162.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000    0.0000 113

 32 omega -162.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -60.0000 113

 33 omega -162.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -180.0000 113

 34 omega -162.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 113

 35 omega -162.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  120.0000 113

 36 omega -162.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 113

 37 omega   30.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  120.0000 39

 38 omega   78.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000   90.0000 80

 39 omega   81.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000    0.0000 77

 40 omega   78.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000   30.0000 80

 41 omega   75.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   90.0000 83

 42 omega   75.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -150.0000 83

 43 omega   78.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  -60.0000 80

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_orient_matrix_UB_11      -0.1596366
_diffrn_orient_matrix_UB_12      0.0576458
_diffrn_orient_matrix_UB_13      -0.0212747
_diffrn_orient_matrix_UB_21      -0.0550307
_diffrn_orient_matrix_UB_22      -0.1450725
_diffrn_orient_matrix_UB_23      -0.0259555
_diffrn_orient_matrix_UB_31      -0.0480204
_diffrn_orient_matrix_UB_32      -0.025349
_diffrn_orient_matrix_UB_33      0.1005458
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22845
_diffrn_reflns_theta_full        71.48
_diffrn_reflns_theta_max         71.48
_diffrn_reflns_theta_min         5.47
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.1856
_exptl_crystal_size_mid          0.1798
_exptl_crystal_size_min          0.1294
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (100%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=-0.000(2), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   -0.006(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0205
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+0.2679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0551
_refine_ls_wR_factor_ref         0.0553
_reflns_number_gt                2383
_reflns_number_total             2405
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4qo00316k2.cif
_cod_data_source_block           a2013225_ir468b
_cod_database_code               1553060