Highly diastereo- and enantioselective synthesis of syn-B-substituted tryptophans via asymmetric Michael addition of a chiral equivalent of nucleophilic glycine and sulfonylindoles
Jiang Wang; Shengbin Zhou; Daizong Lin; Xiao Ding; Hualiang Jiang; Hong Liu; Chem.Commun. 47 (2011) 8355–; doi:10.1039/c1cc12619a

data_7106686
_publ_section_title
;
 Highly diastereo- and enantioselective synthesis of syn-B-substituted
 tryptophans via asymmetric Michael addition of a chiral equivalent of
 nucleophilic glycine and sulfonylindoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              8355
_journal_paper_doi               10.1039/c1cc12619a
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C46 H44 N4 Ni O5'
_chemical_formula_weight         791.56
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.6403(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5816(5)
_cell_length_b                   12.4509(7)
_cell_length_c                   16.5961(9)
_cell_measurement_reflns_used    6996
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.568
_cell_measurement_theta_min      4.493
_cell_volume                     1915.62(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13805
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         6977
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                6527
_reflns_number_total             6977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12619a.txt
_cod_data_source_block           wj_702
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7106686