Completely OH-Selective FeCl3-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans
Ke Zheng; Xiaohua Liu; Song Qin; Mingsheng Xie; Lili Lin; Changwei Hu; Xiaoming Feng; Journal of the American Chemical Society 134 (2012) 17564–17573; doi:10.1021/ja3062002

data_4118796
_publ_section_title
;
 Completely OH-Selective FeCl3-Catalyzed Prins Cyclization: Highly
 Stereoselective Synthesis of 4-OH-Tetrahydropyrans
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17564
_journal_page_last               17573
_journal_paper_doi               10.1021/ja3062002
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 Br O4'
_chemical_formula_sum            'C20 H21 Br O4'
_chemical_formula_weight         405.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-07-08
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.398(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.318(4)
_cell_length_b                   7.5855(7)
_cell_length_c                   10.5790(13)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    144.9
_cell_measurement_theta_max      29.1556
_cell_measurement_theta_min      2.8236
_cell_volume                     1834.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      144.9
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -80.00   -5.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2049  138.0000  159.0000 75

  2 omega  -15.00   12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2049  -77.0000    0.0000 27

  3 omega  -82.00  -33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2049  138.0000  -96.0000 49

  4 omega  -52.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1736  -38.0000  -30.0000 98

  5 omega   49.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1736   77.0000 -120.0000 35

  6 omega  -50.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1736  -77.0000  120.0000 98

  7 omega  -10.00   51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1736   77.0000   30.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0192006000
_diffrn_orient_matrix_UB_12      -0.0022998000
_diffrn_orient_matrix_UB_13      -0.0610474000
_diffrn_orient_matrix_UB_21      0.0243554000
_diffrn_orient_matrix_UB_22      0.0004411000
_diffrn_orient_matrix_UB_23      -0.0308688000
_diffrn_orient_matrix_UB_31      0.0005644000
_diffrn_orient_matrix_UB_32      -0.0934862000
_diffrn_orient_matrix_UB_33      0.0013394000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6701
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.83
_diffrn_source                   'Enhance (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    2.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0138P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0667
_reflns_number_gt                2745
_reflns_number_total             3078
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3062002_si_001.cif
_cod_data_source_block           110708_s1_zk
_cod_database_code               4118796
_chemical_oxdiff_formula         C20H25O3Br1
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32