Syn- and Anti-Selective Prins Cyclizations of δ,ε-Unsaturated Ketones to 1,3-Halohydrins with Lewis Acids
R. Brandon Miles; Chad E. Davis; Robert M. Coates; Journal of Organic Chemistry 71 (2006) 1493–1501; doi:10.1021/jo052142n

data_4021496
_publ_contact_author_address
;Department of Chemistry
University of Illinois
600 South Mathews Avenue, Urbana, IL  61801 (USA)
;
_publ_contact_author_email       coates@scs.uiuc.edu
_publ_contact_author_fax         (+1)217-244-8024
_publ_contact_author_name        'Robert M. Coates'
_publ_section_title
;
 Syn- and Anti-Selective Prins Cyclizations of \d,\e-Unsaturated
 Ketones to 1,3-Halohydrins with Lewis Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1493
_journal_page_last               1501
_journal_paper_doi               10.1021/jo052142n
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C13 H23 Cl O'
_chemical_formula_sum            'C13 H23 Cl O'
_chemical_formula_weight         230.76
_chemical_melting_point          336
_chemical_name_common
(1R,3R,6S,9R)-3-Chloro-5,5,9-trimethylbicyclo[4.4.0]decan-1-ol
_chemical_name_systematic
(1R,3R,6S,9R)-3-Chloro-5,5,9-trimethylbicyclo[4.4.0]decan-1-ol
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2005-07-15   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.748(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.516(4)
_cell_length_b                   8.084(5)
_cell_length_c                   12.148(8)
_cell_measurement_reflns_used    867
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      3.03
_cell_volume                     637.7(7)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  g70gas
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6430
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.68
_diffrn_source                   'normal-focus sealed tube'
_diffrn_standards_decay_%        1.6
_diffrn_standards_interval_time  305
_diffrn_standards_number         57
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_correction_T_min  0.8737
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       tabular
_exptl_crystal_F_000             252
_exptl_crystal_id                g70gas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.4 mm cryo-loop (Hampton Research) with the (1 -1 0) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_recrystallization_method 'evaporation of pentane'
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0291P)^2^+0.0198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                1981
_reflns_number_total             2329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052142nsi20051013_043111.cif
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021496