Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles.
Gonçalves, Carlos R; Lemmerer, Miran; Teskey, Christopher J.; Adler, Pauline; Kaiser, Daniel; Maryasin, Boris; González, Leticia; Maulide, Nuno; Journal of the American Chemical Society 141 (2019) 18437–18443; doi:10.1021/jacs.9b06956

data_4129088
_publ_section_title
;
 Unified Approach to the Chemoselective \a-Functionalization of Amides
 with Heteroatom Nucleophiles.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18437
_journal_page_last               18443
_journal_paper_doi               10.1021/jacs.9b06956
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H23 N3 O3'
_chemical_formula_sum            'C20 H23 N3 O3'
_chemical_formula_weight         353.41
_chemical_name_systematic
;
2-(Methylamino)-2-(4-nitrophenyl)-3-phenyl-1-(pyrrolidin-1-yl)propan-1-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3111(4)
_cell_length_b                   9.3707(5)
_cell_length_c                   30.764(3)
_cell_measurement_reflns_used    2662
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      22.557
_cell_measurement_theta_min      2.545
_cell_volume                     1819.4(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       APEX2
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0713
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            13667
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.340
_diffrn_reflns_theta_min         2.272
_diffrn_source                   'sealed xray tube'
_diffrn_source_type              'Inicoatec IuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_correction_T_min  0.5729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1480 before and 0.0649 after correction. 
The Ratio of minimum to maximum transmission is 0.6452. 
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0265P)^2^+0.7442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2840
_reflns_number_total             3331
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06956_si_002.cif
_cod_data_source_block           mile118_p212121
_cod_depositor_comments          'Adding full bibliography for 4129088.cif.'
_cod_database_code               4129088
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.970