Divergent NHC-Catalyzed Oxidative Transformations of 3-Bromoenal: Selective Synthesis of 2H-Pyran-2-ones and Chiral Dihydropyranones
Gang Wang; Xia Chen; Gaohan Miao; Weijun Yao; Cheng Ma; Journal of Organic Chemistry 78 (2013) 6223–6232; doi:10.1021/jo400950j

data_4028379
_publ_section_title
;
 Divergent NHC-Catalyzed Oxidative Transformations of 3-Bromoenal:
 Selective Synthesis of 2H-Pyran-2-ones and Chiral Dihydropyranones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6223
_journal_page_last               6232
_journal_paper_doi               10.1021/jo400950j
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H13 O3 S'
_chemical_formula_sum            'C12 H13 O3 S'
_chemical_formula_weight         237.28
_chemical_name_systematic
; 
 ? 
;
_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            4
_cell_length_a                   6.6358(3)
_cell_length_b                   6.8047(4)
_cell_length_c                   25.9130(10)
_cell_measurement_reflns_used    3590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4319
_cell_measurement_theta_min      2.9875
_cell_volume                     1170.09(10)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w 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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12148
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9247
_exptl_absorpt_correction_T_min  0.9129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack (1983), 855 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0602
_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^)+(0.1147P)^2^+0.5853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.1921
_reflns_number_gt                1822
_reflns_number_total             2130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400950j_si_001.cif
_cod_data_source_block           111010_10906139
_cod_database_code               4028379