Tuning the Reactivity of Oxygen/Sulfur by Acidity of the Catalyst in Prins Cyclization: Oxa- versus Thia-Selectivity.
Subba Reddy, B. V.; Venkateswarlu, A.; Borkar, Prashant; Yadav, J. S.; Sridhar, B.; Grée, René; The Journal of organic chemistry 79 (2014) 2716–2722; doi:10.1021/jo402832t

data_4029176
_publ_section_title
;
 Tuning the Reactivity of Oxygen/Sulfur by Acidity of the Catalyst in
 Prins Cyclization: Oxa- versus Thia-Selectivity.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2716
_journal_page_last               2722
_journal_paper_doi               10.1021/jo402832t
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C15 H20 O3 S'
_chemical_formula_sum            'C15 H20 O3 S'
_chemical_formula_weight         280.37
_chemical_name_systematic
; 
(3aS*,4R*,7aS*)-4-(2,5-Dimethoxyphenyl)hexahydro-2H-thieno[3,2-c]pyran
;
_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                 105.916(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4466(11)
_cell_length_b                   9.6937(10)
_cell_length_c                   14.9923(16)
_cell_measurement_reflns_used    7532
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.53
_cell_volume                     1460.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  '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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13637
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0547P)^2^+0.5313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                2321
_reflns_number_total             2570
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo402832t_si_001.cif
_cod_data_source_block           ao61m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4029176