Enantioselective (Formal) Aza-Diels-Alder Reactions with Non-Danishefsky-Type Dienes
Uttam K. Tambar; Sharon K. Lee; James L. Leighton; Journal of the American Chemical Society 132 (2010) 10248–10250; doi:10.1021/ja104480g

data_4102773
_publ_section_title
;
 Enantioselective (Formal) Aza-Diels-Alder Reactions with
 Non-Danishefsky-Type Dienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10248
_journal_page_last               10250
_journal_paper_doi               10.1021/ja104480g
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H27 Br N2 O3'
_chemical_formula_weight         423.35
_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                 98.9350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6963(8)
_cell_length_b                   5.6982(4)
_cell_length_c                   13.9991(9)
_cell_measurement_reflns_used    8355
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.36
_cell_volume                     1000.49(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      125(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16151
_diffrn_reflns_theta_full        30.59
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  0.9033
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         6101
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.2884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                5136
_reflns_number_total             6101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja104480g_si_002.cif
_cod_data_source_block           ut17s10
_cod_database_code               4102773