Stereocontrolled Disruption of the Ugi Reaction toward the Production of Chiral Piperazinones: Substrate Scope and Process Development.
Zaretsky, Serge; Adachi, Shinya; Rotstein, Benjamin H.; Hickey, Jennifer L.; Scully, Conor C. G.; St Denis, Jeffrey D.; Courtemanche, Rebecca; Yu, Joy C. Y.; Chung, Benjamin K. W.; Yudin, Andrei K.; The Journal of organic chemistry 79 (2014) 9948–; doi:10.1021/jo5018316

data_4030088
_publ_section_title
;
 Stereocontrolled Disruption of the Ugi Reaction toward the Production of
 Chiral Piperazinones: Substrate Scope and Process Development.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9948
_journal_paper_doi               10.1021/jo5018316
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H27 N3 O2'
_chemical_formula_sum            'C23 H27 N3 O2'
_chemical_formula_weight         377.47
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.090(2)
_cell_length_b                   10.774(3)
_cell_length_c                   21.624(5)
_cell_measurement_reflns_used    9375
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.17
_cell_measurement_theta_min      4.59
_cell_volume                     2117.8(9)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15303
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.285
_diffrn_reflns_theta_min         4.089
_diffrn_source                   'Bruker ImuS'
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1432 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.09(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0363P)^2^+0.3040P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3486
_reflns_number_total             3626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5018316_si_004.cif
_cod_data_source_block           d13120
_cod_depositor_comments
'Adding full bibliography for 4030088--4030090.cif.'
_cod_original_cell_volume        2117.8(10)
_cod_database_code               4030088
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-2