Mild and Highly Enantioselective Vinylogous Aldol Reaction of Brassard's Diene with Aromatic Aldehydes by Combined Lewis Acid Catalyst
Guowei Wang; Jinfeng Zhao; Yuhan Zhou; Baomin Wang; Jingping Qu; Journal of Organic Chemistry 75 (2010) 5326–5329; doi:10.1021/jo100674f

data_4025545
_publ_section_title
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 Mild and Highly Enantioselective Vinylogous Aldol Reaction of Brassard's
 Diene with Aromatic Aldehydes by Combined Lewis Acid Catalyst
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5326
_journal_page_last               5329
_journal_paper_doi               10.1021/jo100674f
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H13 Br O3'
_chemical_formula_weight         297.14
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.719(2)
_cell_length_b                   8.809(3)
_cell_length_c                   21.195(7)
_cell_measurement_reflns_used    2378
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.88
_cell_measurement_theta_min      2.50
_cell_volume                     1254.5(7)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6255
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    3.270
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(10)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0131P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0545
_refine_ls_wR_factor_ref         0.0570
_reflns_number_gt                1862
_reflns_number_total             2198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100674f_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
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_cod_database_code               4025545