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_4036048
_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         'C25 H29 N3 O3'
_chemical_formula_sum            'C25 H29 N3 O3'
_chemical_formula_weight         419.51
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 91.966(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7044(10)
_cell_length_b                   28.659(4)
_cell_length_c                   11.4082(18)
_cell_measurement_reflns_used    4592
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      3.08
_cell_volume                     2190.7(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12614
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        66.765
_diffrn_reflns_theta_max         66.765
_diffrn_reflns_theta_min         3.084
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       rodshape
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.000
_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^+1.2046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.1965
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2695
_reflns_number_total             3756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01936_si_002.cif
_cod_data_source_block           2j
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4036048
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              87634
_shelx_hkl_checksum              56758