Alkylation of Phenylglycinol-Derived Oxazolopiperidone Lactams. Enantioselective Synthesis of β-Substituted Piperidines
Mercedes Amat; Carmen Escolano; Oscar Lozano; Arantxa Gómez-Esqué; Rosa Griera; Elies Molins; Joan Bosch; Journal of Organic Chemistry 71 (2006) 3804–3815; doi:10.1021/jo060157v

data_4021685
_publ_section_title
;
 Alkylation of Phenylglycinol-Derived Oxazolopiperidone Lactams.
 Enantioselective Synthesis of \b-Substituted Piperidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3804
_journal_page_last               3815
_journal_paper_doi               10.1021/jo060157v
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H29 N1 O2'
_chemical_formula_sum            'C28 H29 N O2'
_chemical_formula_weight         411.52
_space_group_IT_number           1
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2004-03-17T16:35:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                89.130(10)
_cell_angle_beta                 73.905(10)
_cell_angle_gamma                61.905(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1830(10)
_cell_length_b                   9.6490(10)
_cell_length_c                   14.829(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    567(2)
_cell_measurement_theta_max      18.51
_cell_measurement_theta_min      11.24
_cell_measurement_wavelength     0.71073
_cell_volume                     1103.3(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      567(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.013571
_diffrn_orient_matrix_UB_12      -0.090477
_diffrn_orient_matrix_UB_13      -0.020384
_diffrn_orient_matrix_UB_21      0.118733
_diffrn_orient_matrix_UB_22      -0.076346
_diffrn_orient_matrix_UB_23      0.002732
_diffrn_orient_matrix_UB_31      -0.050323
_diffrn_orient_matrix_UB_32      -0.007228
_diffrn_orient_matrix_UB_33      0.06779
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5513
_diffrn_reflns_theta_full        27.96
_diffrn_reflns_theta_max         27.96
_diffrn_reflns_theta_min         1.44
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(13)
_refine_ls_extinction_coef       0.075(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         5513
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.1
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.1663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                4587
_reflns_number_total             5513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060157vsi20060124_033715.cif
_cod_original_sg_symbol_Hall     '-P 1'
_cod_original_sg_symbol_H-M      'P -1'
_cod_database_code               4021685