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_1542364
_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_formula_moiety         'C33 H33 N O8 S'
_chemical_formula_sum            'C33 H33 N O8 S'
_chemical_formula_weight         603.66
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.770(3)
_cell_angle_beta                 83.447(3)
_cell_angle_gamma                87.553(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1909(10)
_cell_length_b                   11.4084(10)
_cell_length_c                   14.6334(12)
_cell_measurement_reflns_used    3608
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      2.86
_cell_volume                     1520.9(2)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13638
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.235
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5386
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+2.0528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1991
_reflns_number_gt                3487
_reflns_number_total             5386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03663_si_004.cif
_cod_data_source_block           ch17558
_cod_depositor_comments
'Adding full bibliography for 1542362--1542364.cif.'
_cod_database_code               1542364