Organocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles.
Möhlmann, Lennart; Chang, Geng-Hua; Madhusudhan Reddy, G.; Lee, Chia-Jui; Lin, Wenwei; Organic letters 18 (2016) 688–691; doi:10.1021/acs.orglett.5b03663

data_1542362
_publ_section_title
;
 Organocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones
 via Vinylogous Michael Addition/Henry Reaction Cascade of
 1,3-Indandione-Derived Pronucleophiles.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              688
_journal_page_last               691
_journal_paper_doi               10.1021/acs.orglett.5b03663
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H18 Br N O4'
_chemical_formula_sum            'C25 H18 Br N O4'
_chemical_formula_weight         476.31
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.202(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4822(4)
_cell_length_b                   5.9694(2)
_cell_length_c                   17.3911(7)
_cell_measurement_reflns_used    4230
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.84
_cell_measurement_theta_min      2.44
_cell_volume                     1044.98(7)
_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    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7186
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    2.000
_exptl_absorpt_correction_T_max  0.8405
_exptl_absorpt_correction_T_min  0.6788
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0000P)^2^+0.2420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0606
_reflns_number_gt                2717
_reflns_number_total             3134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03663_si_003.cif
_cod_data_source_block           a17001a
_cod_depositor_comments
'Adding full bibliography for 1542362--1542364.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1542362