Au-catalyzed piperidine synthesis via tandem acyloxy migration/intramolecular [3 + 2] cycloaddition of enynyl esters.
Zheng, Huaiji; Huo, Xing; Zhao, Changgui; Jing, Peng; Yang, Juan; Fang, Bowen; She, Xuegong; Organic letters 13 (2011) 6448–6451; doi:10.1021/ol202746s

data_1502603
_publ_section_title
;
 Au-catalyzed piperidine synthesis via tandem acyloxy
 migration/intramolecular [3 + 2] cycloaddition of enynyl esters.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6448
_journal_page_last               6451
_journal_paper_doi               10.1021/ol202746s
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C30 H33 N O5 S'
_chemical_formula_weight         519.63
_space_group_IT_number           14
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_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                 90.054(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.21(2)
_cell_length_b                   10.072(15)
_cell_length_c                   19.29(3)
_cell_measurement_reflns_used    1175
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.02
_cell_measurement_theta_min      2.28
_cell_volume                     2761(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0992
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_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17534
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.249
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.0702
_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^)+(0.0643P)^2^+0.0687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1758
_reflns_number_gt                2428
_reflns_number_total             4937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202746s_si_003.cif
_cod_data_source_block           p21c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2762(7)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1502603