Synthesis of 3,4-Disubstituted Piperidines by Carbonyl Ene and Prins Cyclizations: Switching between Kinetic and Thermodynamic Control with Brønsted and Lewis Acid Catalysts
Jodi T. Williams; Perdip S. Bahia; Benson M. Kariuki; Neil Spencer; Douglas Philp; John S. Snaith; Journal of Organic Chemistry 71 (2006) 2460–2471; doi:10.1021/jo052532+

data_4021566
_publ_contact_author
;
J.S. Snaith,
School of Chemistry,
University of Birmingham,
Edgbaston, Birmingham, B15 2TT, UK
;
_publ_contact_author_email       j.s.snaith@bham.ac.uk
_publ_section_title
;
 Synthesis of 3,4-Disubstituted Piperidines by Carbonyl Ene and
 Prins Cyclizations: Switching between Kinetic and Thermodynamic
 Control with Br\/onsted and Lewis Acid Catalysts
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2460
_journal_page_last               2471
_journal_paper_doi               10.1021/jo052532+
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C16 H25 Cl N O3.50 S'
_chemical_formula_sum            'C16 H25 Cl N O3.5 S'
_chemical_formula_weight         354.88
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.731(7)
_cell_angle_beta                 94.46(2)
_cell_angle_gamma                78.626(9)
_cell_formula_units_Z            4
_cell_length_a                   11.702(7)
_cell_length_b                   19.771(11)
_cell_length_c                   8.260(3)
_cell_measurement_reflns_used    3234
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      1.78
_cell_volume                     1867.6(17)
_computing_cell_refinement       'MSC software'
_computing_data_collection       'MSC software'
_computing_data_reduction        'MSC software'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SHELXS86
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.761
_diffrn_measured_fraction_theta_max 0.761
_diffrn_measurement_device_type  'Rigaku R-axis IIc image plate'
_diffrn_measurement_method       'Image plate slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8423
_diffrn_reflns_theta_full        25.18
_diffrn_reflns_theta_max         25.18
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_correction_T_min  0.9074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5095
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0903P)^2^+0.2315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.2066
_reflns_number_gt                3234
_reflns_number_total             5095
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052532+si20051209_124751.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C16 H25 Cl N O3.50 S'
_cod_database_code               4021566