Highly enantioselective construction of spiro[4H-pyran-3,3'-oxindoles] through a domino Knoevenagel/Michael/cyclization sequence catalyzed by cupreine.
Chen, Wen-Bing; Wu, Zhi-Jun; Pei, Qing-Lan; Cun, Lin-Feng; Zhang, Xiao-Mei; Yuan, Wei-Cheng; Organic letters 12 (2010) 3132–3135; doi:10.1021/ol1009224

data_1503018
_publ_section_title
;
 Highly enantioselective construction of spiro[4H-pyran-3,3'-oxindoles]
 through a domino Knoevenagel/Michael/cyclization sequence catalyzed by
 cupreine.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3132
_journal_page_last               3135
_journal_paper_doi               10.1021/ol1009224
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H16 Br N3 O4'
_chemical_formula_weight         418.25
_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                   9.1592(3)
_cell_length_b                   11.2121(3)
_cell_length_c                   17.3903(4)
_cell_measurement_reflns_used    10473
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.0609
_cell_measurement_theta_min      2.9568
_cell_volume                     1785.88(9)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26559
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    2.331
_exptl_absorpt_correction_T_max  0.4875
_exptl_absorpt_correction_T_min  0.4558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.354
_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   -0.009(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4078
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0215P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0513
_reflns_number_gt                2637
_reflns_number_total             4078
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1009224_si_002.cif
_cod_data_source_block           ywc20100106-1
_cod_database_code               1503018