High Facial Diastereoselectivity in the Photocycloaddition of a Chiral Aromatic Aldehyde and an Enamide Induced by Intermolecular Hydrogen Bonding
Bach, Thorsten; Bergmann, Hermann; Harms, Klaus; Journal of the American Chemical Society 121 (1999) 10650–10651; doi:10.1021/ja992209m

data_1100584
_publ_contact_author
;
        Thorsten Bach
        Fachbereich Chemie der Universit\"at
        Philipps Universit\"at Marburg
        Hans-Meerwein-Str.
        35032 Marburg
        Bundesrepublik Deutschland
;
_publ_contact_author_fax         '+49 6421 288917 '
_publ_contact_author_phone       '+49 6421 285562 '
_publ_section_title
;
 High Facial Diastereoselectivity in the Photocycloaddition of a Chiral
 Aromatic Aldehyde and an Enamide Induced by Intermolecular Hydrogen Bonding
;
_journal_coden_ASTM              JACSAT
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10650
_journal_page_last               10651
_journal_paper_doi               10.1021/ja992209m
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C24 H30 N2 O5'
_chemical_formula_weight         426.50
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                105.19(1)
_cell_angle_beta                 106.46(1)
_cell_angle_gamma                101.38(1)
_cell_formula_units_Z            2
_cell_length_a                   8.145(1)
_cell_length_b                   11.170(1)
_cell_length_c                   13.241(1)
_cell_measurement_temperature    223(2)
_cell_volume                     1065.85(18)
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4207
_diffrn_reflns_theta_full        69.87
_diffrn_reflns_theta_max         69.87
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.7264
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0041(5)
_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   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0494P)^2^+0.3315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                2872
_reflns_number_total             4021
_reflns_threshold_expression     >2sigma(I)
_cod_database_code               1100584