Organocatalytic Asymmetric Michael Addition of Aliphatic Aldehydes to Indolylnitroalkenes: Access to Contiguous Stereogenic Tryptamine Precursors
Jian Chen; Zhi-Cong Geng; Ning Li; Xiao-Fei Huang; Feng-Feng Pan; Xing-Wang Wang; Journal of Organic Chemistry 78 (2013) 2362–2372; doi:10.1021/jo3024945

data_4028021
_publ_section_title
;
 Organocatalytic Asymmetric Michael Addition of Aliphatic Aldehydes to
 Indolylnitroalkenes: Access to Contiguous Stereogenic Tryptamine
 Precursors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2362
_journal_page_last               2372
_journal_paper_doi               10.1021/jo3024945
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C25 H29 Br N2 O5 S'
_chemical_formula_weight         549.47
_space_group_IT_number           2
_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                70.573(2)
_cell_angle_beta                 80.100(2)
_cell_angle_gamma                81.923(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5291(11)
_cell_length_b                   12.2811(15)
_cell_length_c                   13.3324(16)
_cell_measurement_reflns_used    6124
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.43
_cell_volume                     1292.2(3)
_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      133(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8952
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    1.709
_exptl_absorpt_correction_T_max  0.7599
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5047
_refine_ls_number_restraints     398
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+12.6376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1919
_refine_ls_wR_factor_ref         0.1940
_reflns_number_gt                4626
_reflns_number_total             5047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3024945_si_001.cif
_cod_data_source_block           mo_dm12236_0m
_cod_database_code               4028021