Highly Enantioselective [2+2]-Cycloaddition Reactions Catalyzed by a Chiral Aluminum Bromide Complex
Eda Canales; E. J. Corey; Journal of the American Chemical Society 129 (2007) 12686–12687; doi:10.1021/ja0765262

data_4110089
_publ_section_title
;
 Highly Enantioselective [2+2]-Cycloaddition Reactions Catalyzed by a
 Chiral Aluminum Bromide Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12686
_journal_page_last               12687
_journal_paper_doi               10.1021/ja0765262
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          '(C17 H22 Br N O3) . 0.33333(H2 O)'
_chemical_formula_moiety         'C17 H22 Br N O3, 0.33333(H2 O)'
_chemical_formula_structural     '(C17 H22 Br N O3) 0.33333(H2 O)'
_chemical_formula_sum            'C17 H22.67 Br N O3.33'
_chemical_formula_weight         374.27
_chemical_name_systematic
; 
(1S,7R,8S)-(7-Hydroxybicyclo[5.2.0]nonan-8-yl)methyl
4-Bromophenylcarbamate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.904(1)
_cell_angle_beta                 89.009(1)
_cell_angle_gamma                81.677(1)
_cell_formula_units_Z            6
_cell_length_a                   9.0660(3)
_cell_length_b                   14.5671(5)
_cell_length_c                   20.5696(8)
_cell_measurement_reflns_used    11577
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      23.93
_cell_measurement_theta_min      2.19
_cell_volume                     2594.57(16)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1840 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35702
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.391
_exptl_absorpt_correction_T_max  0.85560
_exptl_absorpt_correction_T_min  0.42063
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1255
_refine_ls_number_reflns         18119
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0699
_reflns_number_gt                14366
_reflns_number_total             18119
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja0765262si20070829_113920.cif
_cod_data_source_block           ejc141
_cod_database_code               4110089