Chiral Phosphine-Catalyzed Enantioselective Construction of γ-Butenolides Through Substitution of Morita-Baylis-Hillman Acetates with 2-Trimethylsilyloxy Furan
Ying-Qing Jiang; Yong-Ling Shi; Min Shi; Journal of the American Chemical Society 130 (2008) 7202–7203; doi:10.1021/ja802422d

data_4107888
_publ_section_title
;
 Chiral Phosphine-Catalyzed Enantioselective Construction of
 \g-Butenolides Through Substitution of Morita-Baylis-Hillman Acetates
 with 2-Trimethylsilyloxy Furan
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7202
_journal_page_last               7203
_journal_paper_doi               10.1021/ja802422d
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H13 Br O3'
_chemical_formula_weight         321.16
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_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                   9.2942(8)
_cell_length_b                   9.2942(8)
_cell_length_c                   16.1873(19)
_cell_measurement_reflns_used    2660
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.012
_cell_measurement_theta_min      5.055
_cell_volume                     1398.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0925
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8271
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    2.940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76883
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       empirical
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0922P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1632
_reflns_number_gt                2511
_reflns_number_total             2981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja802422d-file001.cif
_cod_data_source_block           cd2842
_cod_database_code               4107888