Periselectivity switch of acylketenes in cycloadditions with 1-azadienes: microwave-assisted diastereoselective domino three-component synthesis of α-spiro-δ-lactams.
Presset, Marc; Coquerel, Yoann; Rodriguez, Jean; Organic letters 12 (2010) 4212–4215; doi:10.1021/ol101938r

data_1503242
_publ_section_title
;
 Periselectivity switch of acylketenes in cycloadditions with 1-azadienes:
 microwave-assisted diastereoselective domino three-component synthesis of
 \a-spiro-\d-lactams.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4212
_journal_page_last               4215
_journal_paper_doi               10.1021/ol101938r
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H22 N2 O4'
_chemical_formula_sum            'C23 H22 N2 O4'
_chemical_formula_weight         390.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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      2.4
_audit_creation_date             2010-03-11T11:13:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.221(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.2408(2)
_cell_length_b                   19.6871(4)
_cell_length_c                   19.3546(3)
_cell_measurement_reflns_used    38154
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      1.48
_cell_measurement_wavelength     0.71073
_cell_volume                     3901.23(13)
_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, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38154
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.48
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.56
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         9224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0718
_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^)+(0.1403P)^2^+0.6683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1942
_refine_ls_wR_factor_ref         0.2491
_reflns_number_gt                5650
_reflns_number_total             9224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101938r_si_001.cif
_cod_data_source_block           map5090
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503242