Organocatalytic Enantioselective Synthesis of α-Hydroxyketones through a Friedel-Crafts Reaction of Naphthols and Activated Phenols with Aryl- and Alkylglyoxal Hydrates.
Vila, Carlos; Quintero, Lucia; Blay, Gonzalo; Muñoz, M Carmen; Pedro, José R; Organic letters 18 (2016) 5652–5655; doi:10.1021/acs.orglett.6b02893

data_1555895
_publ_section_title
;
 Organocatalytic Enantioselective Synthesis of \a-Hydroxyketones through a
 Friedel-Crafts Reaction of Naphthols and Activated Phenols with Aryl- and
 Alkylglyoxal Hydrates.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5652
_journal_page_last               5655
_journal_paper_doi               10.1021/acs.orglett.6b02893
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H12 O3 S'
_chemical_formula_weight         284.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4113(2)
_cell_length_b                   10.0776(3)
_cell_length_c                   20.2079(7)
_cell_measurement_reflns_used    7559
_cell_measurement_temperature    250(1)
_cell_measurement_theta_max      28.2200
_cell_measurement_theta_min      3.7510
_cell_volume                     1305.64(7)
_computing_cell_refinement       'CrysAlisPro 2015'
_computing_data_collection       'CrysAlisPro 2015'
_computing_data_reduction        'CrysAlisPro 2015'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      250(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.945
_diffrn_reflns_theta_min         3.334
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.41q'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.2938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                3133
_reflns_number_total             3539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02893_si_001.cif
_cod_data_source_block           shelx
_cod_database_code               1555895
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2014-1
_shelx_res_checksum              33463
_shelx_hkl_checksum              78919