Synthesis and kinetic resolution of substituted tetrahydroquinolines by lithiation then electrophilic quench.
Carter, Nicholas; Li, Xiabing; Reavey, Lewis; Meijer, Anthony J. H. M.; Coldham, Iain; Chemical science 9 (2018) 1352–1357; doi:10.1039/c7sc04435f

data_1548455
_publ_section_title
;
 Synthesis and kinetic resolution of substituted tetrahydroquinolines by
 lithiation then electrophilic quench.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1352
_journal_page_last               1357
_journal_paper_doi               10.1039/c7sc04435f
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-05 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3192(3)
_cell_length_b                   11.0867(4)
_cell_length_c                   17.4057(6)
_cell_measurement_reflns_used    7921
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      4.73
_cell_volume                     1991.31(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25795
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.627
_diffrn_reflns_theta_max         66.627
_diffrn_reflns_theta_min         4.729
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Flack x determined using 1411 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.2781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3382
_reflns_number_total             3512
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04435f2.cif
_cod_data_source_block           carter1_0m
_cod_depositor_comments
'Adding full bibliography for 1548455--1548458.cif.'
_cod_database_code               1548455
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.822
_shelx_estimated_absorpt_t_max   0.876
_shelx_res_checksum              7696