Asymmetric Reduction of Imines with Trichlorosilane, Catalyzed by Sigamide, an Amino Acid-Derived Formamide: Scope and Limitations†
Malkov, Andrei V.; Vranková, Kvetoslava; Stončius, Sigitas; Kočovský, Pavel; The Journal of Organic Chemistry 74 (2009) 5839–5849; doi:10.1021/jo900561h

data_4028953
_publ_section_title
;
 Asymmetric Reduction of Imines with Trichlorosilane, Catalyzed by
 Sigamide, an Amino Acid-Derived Formamide: Scope and Limitations&#x2020;
;
_journal_issue                   16
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              5839
_journal_page_last               5849
_journal_paper_doi               10.1021/jo900561h
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H22 N2 O2'
_chemical_formula_sum            'C19 H22 N2 O2'
_chemical_formula_weight         310.39
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2008-12-15T13:48:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                75.552(2)
_cell_angle_beta                 81.201(2)
_cell_angle_gamma                76.698(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1090(2)
_cell_length_b                   9.8600(4)
_cell_length_c                   15.0310(6)
_cell_measurement_reflns_used    4778
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      1
_cell_measurement_wavelength     0.71073
_cell_volume                     848.83(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.105534
_diffrn_orient_matrix_UB_12      0.20612E-2
_diffrn_orient_matrix_UB_13      -0.579423E-1
_diffrn_orient_matrix_UB_21      -0.123534
_diffrn_orient_matrix_UB_22      -0.92269E-2
_diffrn_orient_matrix_UB_23      -0.333925E-1
_diffrn_orient_matrix_UB_31      -0.467898E-1
_diffrn_orient_matrix_UB_32      0.106484
_diffrn_orient_matrix_UB_33      -0.172203E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4971
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        30.11
_diffrn_reflns_theta_max         30.11
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.2468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                4248
_reflns_number_total             4971
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo900561hsup3.cif
_cod_data_source_block           sg1
_cod_database_code               4028953