1,3-Dioxa-[3,3]-sigmatropic Oxo-Rearrangement of Substituted Allylic Carbamates: Scope and Mechanistic Studies.
Agirre, Maddalen; Henrion, Sylvain; Rivilla, Ivan; Miranda, José I; Cossío, Fernando P; Carboni, Bertrand; Villalgordo, José M; Carreaux, François; The Journal of organic chemistry 83 (2018) 14861–14881; doi:10.1021/acs.joc.8b01320

data_4034751
_publ_section_title
;
 1,3-Dioxa-[3,3]-sigmatropic Oxo-Rearrangement of Substituted Allylic
 Carbamates: Scope and Mechanistic Studies.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14861
_journal_page_last               14881
_journal_paper_doi               10.1021/acs.joc.8b01320
_journal_volume                  83
_journal_year                    2018
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H19 N1 O4 S1'
_chemical_formula_sum            'C18 H19 N O4 S'
_chemical_formula_weight         345.4
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-09T13:21:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-02-20 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                95.356(2)
_cell_angle_beta                 92.661(3)
_cell_angle_gamma                96.203(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6301(4)
_cell_length_b                   12.3190(3)
_cell_length_c                   13.3645(5)
_cell_measurement_reflns_used    5325
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      75.713
_cell_measurement_theta_min      3.602
_cell_measurement_wavelength     1.54184
_cell_volume                     1729.44(10)
_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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_details
;
  1 omega -111.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -37.0000   30.0000 95

  2 omega  -67.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256   37.0000 -150.0000 102

  3 omega    2.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8256 -125.0000   30.0000 77

  4 omega  -49.00  -22.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000 -180.0000 27

  5 omega -157.00  -75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  178.0000  -30.0000 82

  6 omega -113.00  -43.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   61.0000    0.0000 70

  7 omega   88.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 26

  8 omega   37.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 32

  9 omega   37.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 43

 10 omega   52.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 58

 11 omega   55.00  112.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   30.0000 57

 12 omega   47.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -120.0000 53

 13 omega   34.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   60.0000 47

 14 omega  118.00  149.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 31

 15 omega   34.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -180.0000 49

 16 omega   36.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 30

 17 omega   36.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 29

 18 omega   82.00  156.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 74

 19 omega   45.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 37

 20 omega   35.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 33

 21 omega   44.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 33

 22 omega   35.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 34

 23 omega   38.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 39

 24 omega   29.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 76

 25 omega   33.00  148.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   30.0000 115
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.098501
_diffrn_orient_matrix_UB_12      -0.0384541
_diffrn_orient_matrix_UB_13      0.0730821
_diffrn_orient_matrix_UB_21      0.0827592
_diffrn_orient_matrix_UB_22      -0.0269675
_diffrn_orient_matrix_UB_23      -0.0886168
_diffrn_orient_matrix_UB_31      0.0690599
_diffrn_orient_matrix_UB_32      0.1173652
_diffrn_orient_matrix_UB_33      0.0159549
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13169
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.981
_diffrn_reflns_theta_min         3.327
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.847
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.693
_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. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3485
_exptl_crystal_size_mid          0.1094
_exptl_crystal_size_min          0.0525
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         6412
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.3670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                5186
_reflns_number_total             6412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01320_si_002.cif
_cod_data_source_block           a20160195_muestras12
_cod_original_cell_volume        1729.43(9)
_cod_database_code               4034751