Catalytic cross-benzoin/Michael/acetalization cascade for asymmetric synthesis of trifluoromethylated γ-butyrolactones
He, Xiang-Hong; Yang, Lei; Huang, Wei; Zhao, Qian; Pan, Xiao-Li; Jiang, Dao-Feng; Yang, Ming-Cheng; Peng, Cheng; Han, Bo; RSC Adv. 6 (2016) 28960–; doi:10.1039/C6RA03571J

data_7224681
_publ_section_title
;
 Catalytic cross-benzoin/Michael/acetalization cascade for asymmetric
 synthesis of trifluoromethylated \g-butyrolactones
;
_journal_issue                   34
_journal_name_full               'RSC Adv.'
_journal_page_first              28960
_journal_paper_doi               10.1039/C6RA03571J
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H12 Cl F3 O3'
_chemical_formula_sum            'C18 H12 Cl F3 O3'
_chemical_formula_weight         368.73
_chemical_melting_point          350
_chemical_name_common            'chiral (trifluoromethyl)dihydrofuranone'
_chemical_name_systematic
(4S,5S)-5-benzoyl-4-phenyl-5-(trifluoromethyl)dihydrofuran-2(3H)-one
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-12-06 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.997(3)
_cell_length_b                   11.806(4)
_cell_length_c                   17.950(5)
_cell_measurement_reflns_used    7813
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.80
_cell_measurement_theta_min      3.08
_cell_volume                     1694.7(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28499
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         3.077
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/n-hexane'
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 892 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0550P)^2^+0.0411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2551
_reflns_number_total             3893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra03571j2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1694.7(9)
_cod_database_code               7224681
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2013-4
_shelx_res_checksum              95329