Direct, catalytic enantioselective nitroaldol (Henry) reaction of trifluoromethyl ketones: an asymmetric entry to alpha-trifluoromethyl-substituted quaternary carbons.
Tur, Fernando; Saá, José M; Organic letters 9 (2007) 5079–5082; doi:10.1021/ol702434t

data_1505648
_publ_section_title
;
 Direct, catalytic enantioselective nitroaldol (Henry) reaction of
 trifluoromethyl ketones: an asymmetric entry to
 alpha-trifluoromethyl-substituted quaternary carbons.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5079
_journal_page_last               5082
_journal_paper_doi               10.1021/ol702434t
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C9 H10 F3 N O'
_chemical_formula_sum            'C9 H10 F3 N O'
_chemical_formula_weight         205.18
_chemical_melting_point          339
_chemical_name_common            2007ms02jh02d
_chemical_name_systematic
;
 (S)-3-amino-1,1,1-trifluoro-2-phenyl-propan-2-ol
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2007-09-19T12:20:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.877(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2483(4)
_cell_length_b                   5.7003(3)
_cell_length_c                   10.8181(6)
_cell_measurement_reflns_used    1395
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      65.089
_cell_measurement_theta_min      0.883
_cell_measurement_wavelength     1.54178
_cell_volume                     445.36(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo, x2sad, sadabs, xprep, twinlaw and hklf5'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Nonius FR591 KappaCCD2000'
_diffrn_measurement_method       'scans in omega and phi'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0379543
_diffrn_orient_matrix_UB_12      0.1622653
_diffrn_orient_matrix_UB_13      0.0264984
_diffrn_orient_matrix_UB_21      0.0495334
_diffrn_orient_matrix_UB_22      0.0273749
_diffrn_orient_matrix_UB_23      -0.082285
_diffrn_orient_matrix_UB_31      -0.1236059
_diffrn_orient_matrix_UB_32      0.0607952
_diffrn_orient_matrix_UB_33      -0.0336742
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.034
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17879
_diffrn_reflns_theta_full        65.25
_diffrn_reflns_theta_max         65.25
_diffrn_reflns_theta_min         4.1
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.7488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS: Sheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 674 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1525
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.1889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                1492
_reflns_number_total             1525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702434t-file001.cif
_cod_data_source_block           2007ms02
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1505648