Catalytic Asymmetric [3+2] Cycloaddition of Azomethine Ylides. Development of a Versatile Stepwise, Three-Component Reaction for Diversity-Oriented Synthesis
Chuo Chen; Xiaodong Li; Stuart L. Schreiber; Journal of the American Chemical Society 125 (2003) 10174–10175; doi:10.1021/ja036558z

data_4114101
_publ_section_title
;
 Catalytic Asymmetric [3+2] Cycloaddition of Azomethine Ylides.
 Development of a Versatile Stepwise, Three-Component Reaction for
 Diversity-Oriented Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10174
_journal_page_last               10175
_journal_paper_doi               10.1021/ja036558z
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C17 H22 Br N O4'
_chemical_formula_weight         384.27
_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                 108.086(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.1641(13)
_cell_length_b                   5.7004(6)
_cell_length_c                   13.6078(15)
_cell_measurement_temperature    213(2)
_cell_volume                     896.95(17)
_computing_cell_refinement       'SMART (BRUKER, V5.054, 1998)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.01, 1999)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 1998, V5.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5783
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.310
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                3461
_reflns_number_total             3947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036558zsi20030607_051247.cif
_cod_data_source_block           sls74t
_cod_database_code               4114101