Stereoselective synthesis of spiro[tetrahydropyran-3,3'-oxindole] derivatives employing Prins cascade strategy.
Reddy, B. V. Subba; Swathi, V.; Swain, Manisha; Bhadra, Manika Pal; Sridhar, B.; Satyanarayana, D.; Jagadeesh, B.; Organic letters 16 (2014) 6267–6269; doi:10.1021/ol503089m

data_1518431
_publ_section_title
;
 Stereoselective synthesis of spiro[tetrahydropyran-3,3'-oxindole]
 derivatives employing Prins cascade strategy.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6267
_journal_page_last               6269
_journal_paper_doi               10.1021/ol503089m
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C21 H22 F N O4'
_chemical_formula_sum            'C21 H22 F N O4'
_chemical_formula_weight         371.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.785(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.848(3)
_cell_length_b                   12.300(6)
_cell_length_c                   25.729(13)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.65
_cell_measurement_theta_min      2.29
_cell_volume                     1849.8(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scan'
_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  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14106
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0691
_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^)+(0.0649P)^2^+0.9199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                2249
_reflns_number_total             3124
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol503089m_si_001.cif
_cod_data_source_block           aw82m
_cod_depositor_comments          'Adding full bibliography for 1518431.cif.'
_cod_original_cell_volume        1849.6(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1518431