Core-Structure-Motivated Design of a Phosphine-Catalyzed [3 + 2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles
Bin Tan; Nuno R. Candeias; Carlos F. Barbas; Journal of the American Chemical Society 133 (2011) 4672–4675; doi:10.1021/ja110147w

data_4105858
_publ_section_title
;
 Core-Structure-Motivated Design of a Phosphine-Catalyzed [3 + 2]
 Cycloaddition Reaction: Enantioselective Syntheses of
 Spirocyclopenteneoxindoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4672
_journal_page_last               4675
_journal_paper_doi               10.1021/ja110147w
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C35 H27 Cl N2 O6'
_chemical_formula_weight         607.04
_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                 95.244(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8804(4)
_cell_length_b                   10.0970(5)
_cell_length_c                   18.4834(10)
_cell_measurement_reflns_used    5096
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      59.11
_cell_measurement_theta_min      2.40
_cell_volume                     1464.54(13)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7460
_diffrn_reflns_theta_full        59.16
_diffrn_reflns_theta_max         59.16
_diffrn_reflns_theta_min         4.81
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                3030
_reflns_number_total             3383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja110147w_si_001.cif
_cod_data_source_block           barbas11
_cod_database_code               4105858