Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR Products: A Two-Step MCR-Oxidation Protocol toward Functionalized α-Ketoamides and α-Ketotetrazoles.
Foley, Christopher; Shaw, Arthur; Hulme, Christopher; Organic letters 19 (2017) 2238–2241; doi:10.1021/acs.orglett.7b00710

data_1556034
_publ_section_title
;
 Oxidative Deaminations and Deisatinylations of Ugi-Azide and Ugi-3CR
 Products: A Two-Step MCR-Oxidation Protocol toward Functionalized
 \a-Ketoamides and \a-Ketotetrazoles.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2238
_journal_page_last               2241
_journal_paper_doi               10.1021/acs.orglett.7b00710
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H24 N2 O3 Se'
_chemical_formula_sum            'C24 H24 N2 O3 Se'
_chemical_formula_weight         467.41
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.868(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4838(3)
_cell_length_b                   10.5004(4)
_cell_length_c                   21.1264(7)
_cell_measurement_reflns_used    4139
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.87
_cell_volume                     2103.60(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0429
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17080
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.161
_diffrn_reflns_theta_min         1.928
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.814
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0556 before and 0.0447 after correction.
The Ratio of minimum to maximum transmission is 0.8826.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+1.0704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3572
_reflns_number_total             4658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00710_si_002.cif
_cod_data_source_block           mo_foley_cf389f41_0m
_cod_database_code               1556034
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C11(H11), C13(H13), C2(H2), C5(H5), C12(H12), C14(H14),
 C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              94533
_shelx_hkl_checksum              36990
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'