Direct Transformation of N-protected α,β-Unsaturated γ-Amino Amides into γ-Lactams through a Base Mediated Molecular Rearrangement.
Ganesh Kumar, Mothukuri; Veeresh, Kuruva; Nalawade, Sachin A.; Nithun, Raj V.; Gopi, Hosahudya N.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b01936

data_4036049
_publ_section_title
;
 Direct Transformation of N-protected \a,\b-Unsaturated \g-Amino Amides
 into \g-Lactams through a Base Mediated Molecular Rearrangement.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01936
_journal_year                    2019
_chemical_formula_moiety         'C22 H26 N2 O3'
_chemical_formula_sum            'C22 H26 N2 O3'
_chemical_formula_weight         366.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.367(5)
_cell_length_b                   16.811(7)
_cell_length_c                   19.201(8)
_cell_measurement_reflns_used    8470
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.30
_cell_volume                     3992(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.845
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47013
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.532
_diffrn_reflns_theta_min         1.610
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       rodshape
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.665
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.665
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4049
_reflns_number_total             6229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01936_si_002.cif
_cod_data_source_block           2m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036049
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              15257
_shelx_hkl_checksum              31761