Catalytic, Enantioselective Bifunctional Inverse Electron Demand Hetero-Diels-Alder Reactions of Ketene Enolates and o-Benzoquinone Diimides
Ciby J. Abraham; Daniel H. Paull; Michael T. Scerba; James W. Grebinski; Thomas Lectka; Journal of the American Chemical Society 128 (2006) 13370–13371; doi:10.1021/ja065754d

data_4110978
_publ_section_title
;
 Catalytic, Enantioselective Bifunctional Inverse Electron Demand
 Hetero-Diels-Alder Reactions of Ketene Enolates and o-Benzoquinone
 Diimides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13370
_journal_page_last               13371
_journal_paper_doi               10.1021/ja065754d
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C38 H29 Br N2 O4'
_chemical_formula_weight         657.54
_chemical_name_systematic
; 
 ? 
;
_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                 101.900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1342(19)
_cell_length_b                   10.6675(15)
_cell_length_c                   19.582(2)
_cell_volume                     3093.5(7)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_sigmaI/netI    0.1157
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            43133
_diffrn_reflns_resolution_max    0.77
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.72
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  50
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             1368
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     775
_refine_ls_number_reflns         13936
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0466P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                8782
_reflns_number_total             13936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja065754dsi20060808_123432.cif
_cod_data_source_block           x0230
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4110978