Highly Enantio- and Diastereoselective Vinylogous Aldol Reaction by LiCl-Assisted BINOL-Titanium Species.
Wang, Guowei; Wang, Baomin; Qi, Shuai; Zhao, Jinfeng; Zhou, Yuhan; Qu, Jingping; Organic letters 14 (2012) 2734–2737; doi:10.1021/ol300946j

data_1507717
_publ_section_title
;
 Highly Enantio- and Diastereoselective Vinylogous Aldol Reaction by
 LiCl-Assisted BINOL-Titanium Species.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2734
_journal_page_last               2737
_journal_paper_doi               10.1021/ol300946j
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration RR
_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                   8.3264(4)
_cell_length_b                   9.6521(5)
_cell_length_c                   15.9753(9)
_cell_measurement_temperature    273(2)
_cell_volume                     1283.89(12)
_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_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7722
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    3.195
_exptl_absorpt_correction_T_max  0.7201
_exptl_absorpt_correction_T_min  0.4186
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    'riding mode'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0218P)^2^+0.2592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0684
_reflns_number_gt                1890
_reflns_number_total             2208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300946j_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1507717