The catalytic enantioselective synthesis of tetrahydroquinolines containing all-carbon quaternary stereocenters via the formation of aza-ortho-xylylene with 1,2-dihydroquinoline as a precursor.
Li, Guangxun; Liu, Hongxin; Wang, Yingwei; Zhang, Shiqi; Lai, Shujun; Tang, Ling; Zhao, Jinzhong; Tang, Zhuo; Chemical communications (Cambridge, England) 52 (2016) 2304–2306; doi:10.1039/c5cc07752d

data_7118349
_publ_section_title
;
 The catalytic enantioselective synthesis of tetrahydroquinolines
 containing all-carbon quaternary stereocenters via the formation of
 aza-ortho-xylylene with 1,2-dihydroquinoline as a precursor.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2304
_journal_page_last               2306
_journal_paper_doi               10.1039/c5cc07752d
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C29 H32 N2 O4 S'
_chemical_formula_weight         504.62
_chemical_name_systematic
(R)-5,7-dimethoxy-2,2,4-trimethyl-4-(1-tosyl-1H-indol-3-yl)-1,2,3,4-tetrahydroquinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-09-12 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.595(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9590(2)
_cell_length_b                   7.94026(11)
_cell_length_c                   14.0403(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1291.86(4)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12404
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         6.251
_exptl_absorpt_coefficient_mu    1.418
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/isopropanol'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0496P)^2^+0.3945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.557
_reflns_Friedel_fraction_full    0.642
_reflns_Friedel_fraction_max     0.650
_reflns_number_gt                3836
_reflns_number_total             3881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc07752d2.cif
_cod_data_source_block           guoqx2015-9-11a
_cod_depositor_comments          'Adding full bibliography for 7118349.cif.'
_cod_database_code               7118349
_shelxl_version_number           2014-1
_shelx_res_checksum              77035