Remarkable stereoselectivity in intramolecular Borono-Mannich reactions: synthesis of conduramines.
Norsikian, Stéphanie; Soulé, Jean-François; Cannillo, Alexandre; Guillot, Régis; Dau, Marie-Elise Tran Huu; Beau, Jean-Marie; Organic letters 14 (2012) 544–547; doi:10.1021/ol203162s

data_1503559
_publ_section_title
;
 Remarkable stereoselectivity in intramolecular Borono-Mannich reactions:
 synthesis of conduramines.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              544
_journal_page_last               547
_journal_paper_doi               10.1021/ol203162s
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16 H17 N O7'
_chemical_formula_sum            'C16 H17 N O7'
_chemical_formula_weight         335.31
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.2520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8478(2)
_cell_length_b                   6.6488(2)
_cell_length_c                   17.2236(4)
_cell_measurement_reflns_used    6308
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      41.86
_cell_measurement_theta_min      2.37
_cell_volume                     784.18(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20513
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         43.21
_diffrn_reflns_theta_min         1.18
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5001
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+0.0615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                4571
_reflns_number_total             5001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203162s_si_001.cif
_cod_data_source_block           1206GuillotICMMO
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1503559