Synthesis of α-Halo-γ-hydroxyenamides by Titanium Tetrahalide Mediated Addition of Aldehydes or Ketones to Ynamides.
Yabuuchi, Yuto; Kuzuguchi, Takeo; Yoshimura, Tomoyuki; Matsuo, Jun-Ichi; Organic letters 18 (2016) 4951–4953; doi:10.1021/acs.orglett.6b02526

data_1555810
_publ_section_title
;
 Synthesis of \a-Halo-\g-hydroxyenamides by Titanium Tetrahalide Mediated
 Addition of Aldehydes or Ketones to Ynamides.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4951
_journal_page_last               4953
_journal_paper_doi               10.1021/acs.orglett.6b02526
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C17 H18 Cl N O2 S'
_chemical_formula_sum            'C17 H18 Cl N O2 S'
_chemical_formula_weight         335.85
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.9745(18)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   30.1678(18)
_cell_length_b                   8.0311(7)
_cell_length_c                   14.2794(10)
_cell_measurement_reflns_used    10052
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.06
_cell_volume                     3396.4(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15802
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.1494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                2585
_reflns_number_total             3872
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol6b02526_si_001.cif
_cod_data_source_block           yabuuchi50
_cod_database_code               1555810