Asymmetric Synthesis of β2-Tryptophan Analogues via Friedel-Crafts Alkylation of Indoles with a Chiral Nitroacrylate
Nikola Pavlov; Pierre Gilles; Claude Didierjean; Emmanuel Wenger; Emilia Naydenova; Jean Martinez; Monique Calmès; Journal of Organic Chemistry 76 (2011) 6116–6124; doi:10.1021/jo200733t

data_4026478
_publ_section_title
;
 Asymmetric Synthesis of \b2-Tryptophan Analogues via Friedel-Crafts
 Alkylation of Indoles with a Chiral Nitroacrylate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6116
_journal_page_last               6124
_journal_paper_doi               10.1021/jo200733t
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C31 H28 Br1 N3 O7'
_chemical_formula_sum            'C31 H28 Br N3 O7'
_chemical_formula_weight         634.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-03-18T23:57:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.054(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3133(6)
_cell_length_b                   10.1857(4)
_cell_length_c                   14.3493(9)
_cell_measurement_reflns_used    7146
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2681
_cell_measurement_theta_min      3.3948
_cell_measurement_wavelength     0.71073
_cell_volume                     1572.11(15)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
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        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0533617
_diffrn_orient_matrix_UB_12      0.0037675
_diffrn_orient_matrix_UB_13      -0.015929
_diffrn_orient_matrix_UB_21      -0.0324118
_diffrn_orient_matrix_UB_22      -0.0336435
_diffrn_orient_matrix_UB_23      -0.0437185
_diffrn_orient_matrix_UB_31      -0.0211542
_diffrn_orient_matrix_UB_32      0.0608546
_diffrn_orient_matrix_UB_33      -0.02318
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.11
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_limit_h_max       13
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_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23063
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         3.4
_exptl_absorpt_coefficient_mu    1.356
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_description       prism
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.2327
_exptl_crystal_size_mid          0.0417
_exptl_crystal_size_min          0.0226
_platon_squeeze_details
;
;
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.023(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0615P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                4949
_reflns_number_total             6129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200733t_si_002.cif
_cod_data_source_block           11e
_cod_original_cell_volume        1572.11(14)
_cod_database_code               4026478