Highly diastereoselective synthesis of 3-hydroxy-2,2,3-trisubstituted indolines via intramolecular trapping of ammonium ylides with ketones
Changcheng Jing; Dong Xing; Wenhao Hu; Chem.Commun. 50 (2014) 951–; doi:10.1039/c3cc48067d

data_7110267
_publ_section_title
;
 Highly diastereoselective synthesis of 3-hydroxy-2,2,3-trisubstituted
 indolines via intramolecular trapping of ammonium ylides with ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              951
_journal_paper_doi               10.1039/c3cc48067d
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C24 H21 N O3'
_chemical_formula_weight         371.42
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7586(6)
_cell_length_b                   16.5601(10)
_cell_length_c                   21.4710(13)
_cell_measurement_temperature    173(2)
_cell_volume                     3825.3(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41206
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+2.7536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2837
_reflns_number_total             3370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48067d.txt
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7110267