A Heterocycle-Forming Double Michael Reaction. [5 + 1] Annulation Route to Highly Substituted and Functionalized Piperidines
Hughes, Freddie; Grossman, Robert B.; Organic Letters 3 (2001) 2911–; doi:10.1021/ol016395o

data_1507524
_publ_section_title
;
 A Heterocycle-Forming Double Michael Reaction. [5 + 1] Annulation Route
 to Highly Substituted and Functionalized Piperidines
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              2911
_journal_paper_doi               10.1021/ol016395o
_journal_volume                  3
_journal_year                    2001
_chemical_formula_sum            'C17 H23 N3 O5'
_chemical_formula_weight         349.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9260(16)
_cell_length_b                   8.6400(17)
_cell_length_c                   26.257(5)
_cell_measurement_reflns_used    10928
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1795.0(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material
'SHELX97-2 (Sheldrick, 1997) and local procedures'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .969
_diffrn_measured_fraction_theta_max .969
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\w scans at fixed \c = 55\%'
_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    0.0451
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7666
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         .285
_refine_diff_density_min         -.298
_refine_diff_density_rms         .040
_refine_ls_extinction_coef       0.0058(13)
_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   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     416
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.156
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.8239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2381
_reflns_number_total             3065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol016395o_s2.cif
_cod_data_source_block           k01026
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1507524