Synthesis of Six-Membered Spirocyclic Oxindoles with Five Consecutive Stereocenters in an Asymmetric Organocatalytic One-Pot Michael/Michael/Aldol Addition Sequence
Bing Zhou; Yaxi Yang; Jingjing Shi; Zhi Luo; Yuanchao Li; Journal of Organic Chemistry 78 (2013) 2897–2907; doi:10.1021/jo302655u

data_4028069
_publ_section_title
;
 Synthesis of Six-Membered Spirocyclic Oxindoles with Five Consecutive
 Stereocenters in an Asymmetric Organocatalytic One-Pot
 Michael/Michael/Aldol Addition Sequence
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2897
_journal_page_last               2907
_journal_paper_doi               10.1021/jo302655u
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H28 Cl N3 O8'
_chemical_formula_weight         630.03
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 110.755(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3104(9)
_cell_length_b                   32.937(3)
_cell_length_c                   11.4746(12)
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.87
_cell_measurement_theta_min      4.50
_cell_volume                     2937.0(5)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21553
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.9926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             1298
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.253
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.30(18)
_refine_ls_extinction_coef       0.138(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.447
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     822
_refine_ls_number_reflns         8600
_refine_ls_number_restraints     848
_refine_ls_restrained_S_all      1.385
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.1325
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3514
_refine_ls_wR_factor_ref         0.3639
_reflns_number_gt                6597
_reflns_number_total             8600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302655u_si_002.cif
_cod_data_source_block           2013034_0m.CIF
_cod_database_code               4028069