Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine.
Si, Chang-Mei; Mao, Zhuo-Ya; Dong, Han-Qing; Du, Zhen-Ting; Wei, Bang-Guo; Lin, Guo-Qiang; The Journal of organic chemistry 80 (2015) 5824–5833; doi:10.1021/acs.joc.5b00803

data_4031019
_publ_section_title
;
 Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones:
 Syntheses of (-)-Epiquinamide and (+)-Swainsonine.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5824
_journal_page_last               5833
_journal_paper_doi               10.1021/acs.joc.5b00803
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H34 Cl N O4 Si'
_chemical_formula_weight         464.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 112.415(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.902(9)
_cell_length_b                   11.579(9)
_cell_length_c                   11.064(9)
_cell_measurement_reflns_used    3247
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.594
_cell_measurement_theta_min      4.463
_cell_volume                     1291.1(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7826
_diffrn_reflns_point_group_measured_fraction_full 0.869
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.991
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 1435 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4404
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0941P)^2^+0.0447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.723
_reflns_Friedel_fraction_max     0.713
_reflns_number_gt                3999
_reflns_number_total             4404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00803_si_001.cif
_cod_data_source_block           cd214295
_cod_depositor_comments
'Adding full bibliography for 4031018--4031019.cif.'
_cod_original_cell_volume        1291.2(18)
_cod_database_code               4031019
_shelxl_version_number           2013-4
_shelx_res_checksum              39798
_shelx_hkl_checksum              33932