Iminium ion catalysis: the enantioselective Friedel-Crafts alkylation-acetalization cascade of naphthols with alpha,beta-unsaturated cyclic ketones
Enrico Paradisi; Paolo Righi; Andrea Mazzanti; Silvia Ranieri; Giorgio Bencivenni; Chem.Commun. 48 (2012) 11178–; doi:10.1039/c2cc35582e

data_7108565
_publ_section_title
;
 Iminium ion catalysis: the enantioselective Friedel-Crafts
 alkylation-acetalization cascade of naphthols with alpha,beta-unsaturated
 cyclic ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              11178
_journal_paper_doi               10.1039/c2cc35582e
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_sum            'C22 H20 O2'
_chemical_formula_weight         316.38
_chemical_name_common            'compound 6da'
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             07/30/2012
_audit_creation_method           SHELXL-97
_audit_update_record             07/31/2012
_cell_angle_alpha                90.00
_cell_angle_beta                 123.3630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.582(3)
_cell_length_b                   6.4957(10)
_cell_length_c                   15.898(2)
_cell_measurement_reflns_used    160
_cell_measurement_temperature    296(2)
_cell_volume                     1689.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Phi and Omega 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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9738
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3846
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.3168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                3296
_reflns_number_total             3846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc35582e.txt
_cod_data_source_block           gb1642-chirale
_cod_original_cell_volume        1688.9(4)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7108565