An Efficient Synthesis of Enantiomerically Enriched Trifluoromethylated 1,2-Diols and 1,2-Amino Alcohols with Quaternary Stereocenters by Diastereoselective Addition of TMSCF~3~ to Chiral 2-Acyl-1,3-perhydrobenzoxazines
Rafael Pedrosa; Sonia Sayalero; Martina Vicente; Alicia Maestro; Journal of Organic Chemistry 71 (2006) 2177–2180; doi:10.1021/jo052458v

data_4021541
_publ_section_title
;
 An Efficient Synthesis of Enantiomerically Enriched Trifluoromethylated
 1,2-Diols and 1,2-Amino Alcohols with Quaternary Stereocenters
 by Diastereoselective Addition of TMSCF~3~ to Chiral
 2-Acyl-1,3-perhydrobenzoxazines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2177
_journal_page_last               2180
_journal_paper_doi               10.1021/jo052458v
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_sum            'C24 H36 F3 N O2'
_chemical_formula_weight         427.54
_chemical_name_systematic
;
(2S,2'S,4a'S,7'R,8a'R)-2-(3-Benzyl-4',4',7'-
trimethyl-octahydro-2H-benzo[e][1,3] oxazin-2'-yl)-1,1,1-trifluorohexan-2-
ol
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.718(6)
_cell_angle_beta                 74.078(6)
_cell_angle_gamma                63.603(5)
_cell_formula_units_Z            1
_cell_length_a                   8.220(3)
_cell_length_b                   9.013(3)
_cell_length_c                   9.635(3)
_cell_measurement_temperature    298(2)
_cell_volume                     590.3(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3217
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             230
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.060
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+0.0332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                3096
_reflns_number_total             3217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052458vsi20060125_090812_3.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_database_code               4021541