Catalytic Asymmetric Addition of Alcohols to Imines: Enantioselective Preparation of Chiral N,O-Aminals
Guilong Li; Frank R. Fronczek; Jon C. Antilla; Journal of the American Chemical Society 130 (2008) 12216–12217; doi:10.1021/ja8033334

data_4108338
_publ_contact_author_address
;
Department of Chemistry, University of South Florida, 
4202 East Fowler Avenue CHE205A, Tampa, Florida 33620
;
_publ_contact_author_email       jantilla@cas.usf.edu
_publ_contact_author_name        'Jon C. Antilla'
_publ_contact_author_phone       813-974-7438
_publ_section_title
;
 Catalytic Asymmetric Addition of Alcohols to Imines: Enantioselective
 Preparation of Chiral N,O-Aminals
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12216
_journal_page_last               12217
_journal_paper_doi               10.1021/ja8033334
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration R
_chemical_formula_moiety         'C16 H16 Cl N O2'
_chemical_formula_sum            'C16 H16 Cl N O2'
_chemical_formula_weight         289.75
_chemical_melting_point          394(1)
_chemical_name_common            (R)-N-((2-chloroethoxy)(phenyl)methyl)benzamide
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0990(10)
_cell_length_b                   11.694(2)
_cell_length_c                   23.476(5)
_cell_measurement_reflns_used    1895
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.5
_cell_volume                     1399.8(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare  et al., 1999)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'KappaCCD (with Oxford Cryostream)'
_diffrn_measurement_method       ' \w scans with \k offsets'
_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  0.078
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10988
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         27.9
_diffrn_reflns_theta_min         3.1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.31
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack (1983) '
_refine_ls_abs_structure_Flack   -0.13(8)
_refine_ls_extinction_coef       0.0069(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   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.086
_refine_ls_R_factor_gt           0.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0166P)^2^+0.7580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.078
_refine_ls_wR_factor_ref         0.089
_reflns_number_gt                2520
_reflns_number_total             3318
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja8033334_si_003.cif
_cod_data_source_block           2-258
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4108338