Metal-Free Brønsted Acid Catalyzed Formal [3 + 3] Annulation. Straightforward Synthesis of Dihydro-2H-Chromenones, Pyranones, and Tetrahydroquinolinones
Julie Moreau; Claudie Hubert; Jessika Batany; Loic Toupet; Thierry Roisnel; Jean-Pierre Hurvois; Jean-Luc Renaud; Journal of Organic Chemistry 74 (2009) 8963–8973; doi:10.1021/jo901238y

data_4025075
_publ_contact_author             'Roisnel, Thierry'
_publ_contact_author_email       thierry.roisnel@univ-rennes1.fr
_publ_section_title
;
Metal-Free Br\/onsted Acid Catalyzed Formal [3 + 3] Annulation.
Straightforward Synthesis of Dihydro-2H-Chromenones, Pyranones, and
Tetrahydroquinolinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8963
_journal_page_last               8973
_journal_paper_doi               10.1021/jo901238y
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H20 O2'
_chemical_formula_sum            'C16 H20 O2'
_chemical_formula_weight         244.32
_space_group_IT_number           19
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2008-12-02T18:03:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0871(3)
_cell_length_b                   8.8078(5)
_cell_length_c                   24.0887(11)
_cell_measurement_reflns_used    5077
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.46
_cell_measurement_wavelength     0.71073
_cell_volume                     1291.49(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20652
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.16
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.3386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                1705
_reflns_number_total             1726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901238y_si_002.cif
_cod_data_source_block           JM437
_cod_database_code               4025075