N-heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles.
Xu, Jianfeng; Mou, Chengli; Zhu, Tingshun; Song, Bao-An; Chi, Yonggui Robin; Organic letters 16 (2014) 3272–3275; doi:10.1021/ol501286e

data_1516464
_publ_section_title
;
 N-heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin
 reaction of enals with isatin-derived ketimines: access to chiral
 quaternary aminooxindoles.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3272
_journal_page_last               3275
_journal_paper_doi               10.1021/ol501286e
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H30 Cl N2 O4'
_chemical_formula_weight         469.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 92.662(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.651(5)
_cell_length_b                   8.9952(16)
_cell_length_c                   13.072(3)
_cell_measurement_reflns_used    1862
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      19.5960
_cell_measurement_theta_min      2.3889
_cell_volume                     2543.1(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_sigmaI/netI    0.1033
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29143
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.180
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_refine_diff_density_max         0.185
_refine_diff_density_min         -0.236
_refine_ls_abs_structure_details
;
Flack x determined using 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         5201
_refine_ls_number_restraints     1659
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0613P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                2852
_reflns_number_total             5201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501286e_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1516464.cif.'
_cod_original_cell_volume        2543.1(8)
_cod_database_code               1516464
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