Stereoselective synthesis of 2,3-disubstituted indoline, pyrrolidine and cyclic ether-fused 1,2-dihydroquinoline derivatives using alkyne iminium ion cyclization of vinylogous carbamates: switch of regioselectivity using an internal hydroxy group as a nucleophile
Santosh J. Gharpure; V. Prasath; Vinod Kumar; Chem.Commun. 51 (2015) 13623–; doi:10.1039/C5cc05292K

data_7117681
_publ_section_title
;
 Stereoselective synthesis of 2,3-disubstituted indoline, pyrrolidine and
 cyclic ether-fused 1,2-dihydroquinoline derivatives using alkyne iminium
 ion cyclization of vinylogous carbamates: switch of regioselectivity
 using an internal hydroxy group as a nucleophile
;
_journal_name_full               Chem.Commun.
_journal_page_first              13623
_journal_paper_doi               10.1039/C5cc05292K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C17 H21 N O5 S'
_chemical_formula_sum            'C17 H21 N O5 S'
_chemical_formula_weight         351.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-06-25 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.288(11)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   13.648(5)
_cell_length_b                   8.763(3)
_cell_length_c                   14.280(6)
_cell_measurement_reflns_used    1558
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.50
_cell_measurement_theta_min      6.70
_cell_volume                     1707.4(11)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54190
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8397
_diffrn_reflns_theta_full        68.47
_diffrn_reflns_theta_max         68.47
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744.00
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.950
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1541P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2492
_reflns_number_gt                2145
_reflns_number_total             3113
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5cc05292k2.cif
_cod_data_source_block           SJG-VPS-10-18-A-1
_cod_original_cell_volume        1707.4(12)
_cod_database_code               7117681