Stereoselective Construction of Halogenated Quaternary Stereogenic Centers via Catalytic Asymmetric Diels-Alder Reaction
Kazutaka Shibatomi; Kentaro Futatsugi; Fumito Kobayashi; Seiji Iwasa; Hisashi Yamamoto; Journal of the American Chemical Society 132 (2010) 5625–5627; doi:10.1021/ja1018628

data_4102351
_publ_section_title
;
 Stereoselective Construction of Halogenated Quaternary Stereogenic
 Centers via Catalytic Asymmetric Diels-Alder Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5625
_journal_page_last               5627
_journal_paper_doi               10.1021/ja1018628
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H21 Br O2'
_chemical_formula_weight         361.27
_space_group_IT_number           4
_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                 92.797(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0708(15)
_cell_length_b                   16.433(3)
_cell_length_c                   13.370(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1551.7(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18576
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    2.654
_exptl_absorpt_correction_T_max  0.588
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
absorption corrections were made based on correspondance of
equivalent intensities usingprogram SADABS (G. Sheldrick, Bruker 
Analytical X-ray Systems, Madison, WI)
;
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.242
_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   0.004(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         7433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0312P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0600
_reflns_number_gt                6894
_reflns_number_total             7433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1018628_si_002.cif
_cod_data_source_block           kent01s
_cod_original_cell_volume        1551.6(6)
_cod_database_code               4102351