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_4105859
_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            'C30 H32 Cl N O7'
_chemical_formula_weight         554.02
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   9.4000(18)
_cell_length_b                   10.1544(19)
_cell_length_c                   30.775(6)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.27
_cell_volume                     2937.5(10)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \w 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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            25041
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       Block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         6715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+0.5093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                6304
_reflns_number_total             6715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja110147w_si_002.cif
_cod_data_source_block           Barbas12
_cod_database_code               4105859