Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch
John D. Huber; James L. Leighton; Journal of the American Chemical Society 129 (2007) 14552–14553; doi:10.1021/ja076035h

data_4110248
_publ_section_title
;
 Highly Enantioselective Imine Cinnamylation with a Remarkable
 Diastereochemical Switch
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14552
_journal_page_last               14553
_journal_paper_doi               10.1021/ja076035h
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H18 Br N O2'
_chemical_formula_weight         420.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 90.99(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9870(14)
_cell_length_b                   24.587(5)
_cell_length_c                   11.022(2)
_cell_measurement_temperature    100(2)
_cell_volume                     1893.2(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\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  0.1061
_diffrn_reflns_av_sigmaI/netI    0.0973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20006
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    2.189
_exptl_absorpt_correction_T_max  0.9175
_exptl_absorpt_correction_T_min  0.3957
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   numerical
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.274
_refine_diff_density_min         -1.166
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 3933 Friedel pairs'
_refine_ls_abs_structure_Flack   0.069(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8316
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0779
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+6.9049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.1781
_reflns_number_gt                6886
_reflns_number_total             8316
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja076035hsi20070810_031422.cif
_cod_data_source_block           x1589l
_cod_database_code               4110248