Highly stereoselective TiCl4-Catalyzed Evans-aldol and Et3Al-mediated Reformatsky reactions. Efficient accesses to optically active syn- or anti-alpha-trifluoromethyl-beta-hydroxy carboxylic acid derivatives.
Shimada, Taichi; Yoshioka, Masamitsu; Konno, Tsutomu; Ishihara, Takashi; Organic letters 8 (2006) 1129–1131; doi:10.1021/ol0531435

data_1505877
_publ_section_title
;
 Highly stereoselective TiCl4-Catalyzed Evans-aldol and Et3Al-mediated
 Reformatsky reactions. Efficient accesses to optically active syn- or
 anti-alpha-trifluoromethyl-beta-hydroxy carboxylic acid derivatives.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1129
_journal_page_last               1131
_journal_paper_doi               10.1021/ol0531435
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C21 H20 F3 N O5 '
_chemical_formula_sum            'C21 H20 F3 N O5'
_chemical_formula_weight         423.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 98.24(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.779(3)
_cell_length_b                   5.731(1)
_cell_length_c                   9.827(2)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    198.1
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      25.0
_cell_volume                     991.0(3)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  SHELXL
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2681
_diffrn_reflns_theta_full        66.75
_diffrn_reflns_theta_max         66.75
_diffrn_standards_decay_%        1.23
_diffrn_standards_interval_count 0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             440.00
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     353
_refine_ls_number_reflns         1953
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.0712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                2395
_reflns_number_total             2678
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol0531435si20060130_091706.cif
_cod_data_source_block           '_Yoshi-01'
_cod_original_formula_sum        'C21 H20 F3 N O5 '
_cod_database_code               1505877