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_7108564
_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 ad
_chemical_formula_sum            'C20 H15 Cl O3'
_chemical_formula_weight         338.77
_chemical_name_common
;(S)-5-chloro-3-(2-hydroxy-6-methoxynaphthalen-1-yl)-2,3-
dihydro-1H-inden-1-one
;
_chemical_name_systematic
;
(S)-5-chloro-3-(2-hydroxy-6-methoxynaphthalen-1-yl)-2,3-dihydro-1H-inden-1-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_date             07/17/2012
_audit_creation_method           SHELXL-97
_audit_update_record             09/03/2012
_cell_angle_alpha                90.00
_cell_angle_beta                 92.146(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6325(13)
_cell_length_b                   8.6693(13)
_cell_length_c                   22.017(3)
_cell_measurement_reflns_used    201
_cell_measurement_temperature    296(2)
_cell_volume                     1646.5(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 0.998
_diffrn_measured_fraction_theta_max 0.992
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18838
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9078
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         7373
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0646P)^2^+0.0569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                5444
_reflns_number_total             7373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc35582e.txt
_cod_data_source_block           gb1626-chirale
_cod_original_cell_volume        1646.6(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7108564