Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: a new entry to sulfur-containing chiral quaternary carbons.
Sakakura, Akira; Yamada, Hiroki; Ishihara, Kazuaki; Organic letters 14 (2012) 2972–2975; doi:10.1021/ol300921f

data_1507812
_publ_section_title
;
 Enantioselective Diels-Alder reaction of \a-(acylthio)acroleins: a new
 entry to sulfur-containing chiral quaternary carbons.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2972
_journal_page_last               2975
_journal_paper_doi               10.1021/ol300921f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C21 H26 F N O2 S'
_chemical_formula_weight         375.49
_chemical_name_common
;
2-Formyl-3-(4-fluorophenyl)bicyclo[2.2.1]hept-5-en-2-yl carbamothioate
;
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           triclinic
_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                 102.781(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1417(17)
_cell_length_b                   14.590(3)
_cell_length_c                   17.092(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1980.0(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14043
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9725
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.062
_refine_diff_density_min         -1.335
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         9250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          11.250
_refine_ls_shift/su_mean         0.358
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1491P)^2^+1.9592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.2071
_reflns_number_gt                8067
_reflns_number_total             9250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300921f_si_002.cif
_cod_data_source_block           hya1
_cod_depositor_comments          'Adding full bibliography for 1507812.cif.'
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1507812