Asymmetric Vinylogous Aldol Reaction of Silyloxy Furans with a Chiral Organic Salt
Ravi P. Singh; Bruce M. Foxman; Li Deng; Journal of the American Chemical Society 132 (2010) 9558–9560; doi:10.1021/ja103331t

data_4102673
_publ_section_title
;
 Asymmetric Vinylogous Aldol Reaction of Silyloxy Furans with a Chiral
 Organic Salt
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9558
_journal_page_last               9560
_journal_paper_doi               10.1021/ja103331t
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H9 Br1 O3'
_chemical_formula_sum            'C11 H9 Br O3'
_chemical_formula_weight         269.09
_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
_audit_creation_date             09-09-23
_audit_creation_method           CRYSTALS_ver_12.87
_cell_angle_alpha                90
_cell_angle_beta                 91.456(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3946(4)
_cell_length_b                   7.6287(5)
_cell_length_c                   12.9305(8)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    120
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     531.97(6)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'CRYSTALS (Betteridge et al., 2003)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19419
_diffrn_reflns_theta_full        29.996
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         1.575
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.846
_exptl_absorpt_correction_T_max  0.45
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.522
_exptl_crystal_size_mid          0.373
_exptl_crystal_size_min          0.209
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.68
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.007(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0342
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0164
_refine_ls_R_factor_gt           0.0157
_refine_ls_shift/su_max          0.0146033
_refine_ls_shift/su_mean         3.2914422
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.08P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0400
_refine_ls_wR_factor_gt          0.0391
_refine_ls_wR_factor_ref         0.0400
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3026
_reflns_number_total             3111
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.91
_oxford_diffrn_Wilson_scale      14.66
_oxford_refine_ls_r_factor_ref   0.0164
_oxford_refine_ls_scale          0.26489(11)
_oxford_reflns_number_all        3111
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'RPS_VI_6_A1_0m in P2(1)'
_cod_data_source_file            ja103331t_si_003.cif
_cod_data_source_block           rps_vi_6_a1
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C11 H9 Br1 O3'
_cod_database_code               4102673