Enantioselective Three-Component Amination of Enecarbamates Enables the Synthesis of Structurally Complex Small Molecules.
Dumoulin, Audrey; Bernadat, Guillaume; Masson, Géraldine; The Journal of organic chemistry 82 (2017) 1775–1789; doi:10.1021/acs.joc.6b03093

data_4032154
_publ_section_title
;
 Enantioselective Three-Component Amination of Enecarbamates Enables the
 Synthesis of Structurally Complex Small Molecules.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1775
_journal_page_last               1789
_journal_paper_doi               10.1021/acs.joc.6b03093
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C27 H30 N2 O6'
_chemical_formula_sum            'C27 H30 N2 O6'
_chemical_formula_weight         478.53
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.680(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3517(5)
_cell_length_b                   10.7780(5)
_cell_length_c                   21.8140(11)
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.8110
_cell_measurement_theta_min      3.9640
_cell_volume                     2425.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_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      200
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -98.00  82.00   0.50   20.00    --   -8.00 -24.00 -36.00  360
  2  \w    -49.00  34.00   0.50   20.00    --   -8.00 -56.00   0.00  166
  3  \w    -10.00  43.50   0.50   20.00    --   -8.00  72.00   0.00  107
  4  \w      4.00  49.00   0.50   20.00    --   -8.00  56.00-144.00   90
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0343559000
_diffrn_orient_matrix_UB_12      -0.0287237000
_diffrn_orient_matrix_UB_13      -0.0256722000
_diffrn_orient_matrix_UB_21      -0.0072095000
_diffrn_orient_matrix_UB_22      -0.0544236000
_diffrn_orient_matrix_UB_23      0.0177140000
_diffrn_orient_matrix_UB_31      -0.0590593000
_diffrn_orient_matrix_UB_32      0.0233274000
_diffrn_orient_matrix_UB_33      0.0096426000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25782
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.895
_diffrn_reflns_theta_min         5.022
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.1428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4526
_reflns_number_total             6186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b03093_si_002.cif
_cod_data_source_block           03032016_ad_mo
_cod_depositor_comments          'Adding full bibliography for 4032154.cif.'
_cod_database_code               4032154
_reflns_odcompleteness_completeness 88.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.83
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1 = N7-H7
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1a), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C25(H25)
3.d Idealised Me refined as rotating group:
 C3(H3a,H3b,H3c), C21(H21a,H21b,H21c), C24(H24a,H24b,H24c), C27(H27a,H27b,H27c)
;
_shelx_res_checksum              21685
_shelx_hkl_checksum              41764
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.824
_oxdiff_exptl_absorpt_empirical_full_min 0.558