Stereodefined N,O-Acetals: Pd-Catalyzed Synthesis from Homopropargylic Amines and Utility in the Flexible Synthesis of 2,6-Substituted Piperidines
Haejin Kim; Young Ho Rhee; Journal of the American Chemical Society 134 (2012) 4011–4014; doi:10.1021/ja2116298

data_4117585
_publ_section_title
;
 Stereodefined N,O-Acetals: Pd-Catalyzed Synthesis from Homopropargylic
 Amines and Utility in the Flexible Synthesis of 2,6-Substituted
 Piperidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4011
_journal_page_last               4014
_journal_paper_doi               10.1021/ja2116298
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H33 N O3 S Si'
_chemical_formula_weight         455.67
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 117.214(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.543(2)
_cell_length_b                   7.6021(9)
_cell_length_c                   19.030(3)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.191
_cell_measurement_theta_min      3.086
_cell_volume                     2514.3(6)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  'Diamond 3.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX II'
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            35501
_diffrn_reflns_theta_full        36.68
_diffrn_reflns_theta_max         36.68
_diffrn_reflns_theta_min         1.20
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9920
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.137
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         11687
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                9535
_reflns_number_total             11687
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2116298_si_001.cif
_cod_data_source_block           c2
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4117585