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_4117586
_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            'C21 H23 N O3 S'
_chemical_formula_weight         369.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3294(5)
_cell_length_b                   14.2360(12)
_cell_length_c                   20.5165(15)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.241
_cell_measurement_theta_min      3.305
_cell_volume                     1848.6(3)
_computing_cell_refinement       'Bruekr APEX II'
_computing_data_collection       'Bruekr APEX II'
_computing_data_reduction        'Bruekr 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 0.968
_diffrn_measured_fraction_theta_max 0.968
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            42453
_diffrn_reflns_theta_full        42.68
_diffrn_reflns_theta_max         42.68
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_correction_T_min  0.8751
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         12600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0610P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                9617
_reflns_number_total             12600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2116298_si_002.cif
_cod_data_source_block           p212121
_cod_database_code               4117586