Indium-Mediated Diastereoselective Allylation of D- and L-Glyceraldimines with 4-Bromo-1,1,1-trifluoro-2-butene: Highly Stereoselective Synthesis of 4,4,4-Trifluoroisoleucines and 4,4,4-Trifluorovaline
Qi Chen; Xiao-Long Qiu; Feng-Ling Qing; Journal of Organic Chemistry 71 (2006) 3762–3767; doi:10.1021/jo0601157

data_4021681
_publ_section_title
;
 Indium-Mediated Diastereoselective Allylation of D- and
 L-Glyceraldimines with 4-Bromo-1,1,1-trifluoro-2-butene:
 Highly Stereoselective Synthesis of 4,4,4-Trifluoroisoleucines
 and 4,4,4-Trifluorovaline
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3762
_journal_page_last               3767
_journal_paper_doi               10.1021/jo0601157
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration uk
_chemical_formula_sum            'C17 H18 F3 N O6'
_chemical_formula_weight         389.32
_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                   6.5866(7)
_cell_length_b                   10.7519(11)
_cell_length_c                   25.662(3)
_cell_measurement_reflns_used    2131
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.206
_cell_measurement_theta_min      4.943
_cell_volume                     1817.3(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1205
_diffrn_reflns_av_sigmaI/netI    0.0982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10786
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63633
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.415
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_extinction_coef       0.0018(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0402P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                2280
_reflns_number_total             3971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0601157si20060119_052917.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4021681