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_7117678
_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         'C27 H27 N O5 S'
_chemical_formula_sum            'C27 H27 N O5 S'
_chemical_formula_weight         477.57
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_update_record
;
2015-06-25 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                99.142(9)
_cell_angle_beta                 109.67(4)
_cell_angle_gamma                102.46(2)
_cell_formula_units_Z            2
_cell_length_a                   9.687(13)
_cell_length_b                   10.731(8)
_cell_length_c                   12.624(12)
_cell_measurement_reflns_used    1251
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.70
_cell_measurement_theta_min      7.00
_cell_volume                     1168(2)
_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    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8748
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.561
_exptl_absorpt_correction_T_max  0.732
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3834
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0741P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                2759
_reflns_number_total             3835
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5cc05292k2.cif
_cod_data_source_block           SJG-VPS-NTS-CYS-4
_cod_original_cell_volume        1168(3)
_cod_database_code               7117678