Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.
Du, Xiang-Wei; Stanley, Levi M.; Organic letters 17 (2015) 3276–3279; doi:10.1021/acs.orglett.5b01447

data_1520637
_publ_section_title
;
 Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective
 Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated
 Derivatives.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3276
_journal_page_last               3279
_journal_paper_doi               10.1021/acs.orglett.5b01447
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C21 H15 F O2'
_chemical_formula_weight         318.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 103.2460(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0845(12)
_cell_length_b                   5.9453(6)
_cell_length_c                   22.597(2)
_cell_measurement_temperature    173.(2)
_cell_volume                     1580.3(3)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2013)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2013)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2013)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173.(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ' full spere \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16221
_diffrn_reflns_theta_full        28.74
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'X-ray tuve'
_diffrn_source_type              'Sealed tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0687P)^2^+0.3053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                3166
_reflns_number_total             4079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01447_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1520637.cif.'
_cod_database_code               1520637