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_4030090
_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         'C34 H35 N3 O2'
_chemical_formula_sum            'C34 H35 N3 O2'
_chemical_formula_weight         517.65
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.437(3)
_cell_angle_beta                 91.851(3)
_cell_angle_gamma                90.341(3)
_cell_formula_units_Z            1
_cell_length_a                   6.3049(4)
_cell_length_b                   7.6994(5)
_cell_length_c                   14.4602(8)
_cell_measurement_reflns_used    6000
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.37
_cell_measurement_theta_min      6.27
_cell_volume                     685.07(7)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker ImuS'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6344
_diffrn_reflns_theta_full        66.36
_diffrn_reflns_theta_max         66.36
_diffrn_reflns_theta_min         6.27
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.0422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                2609
_reflns_number_total             2628
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5018316_si_003.cif
_cod_data_source_block           d12290
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030088--4030090.cif.
;
_cod_database_code               4030090