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_4021539
_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            'C27 H34 F3 N O3'
_chemical_formula_weight         477.55
_chemical_name_systematic
;
(1S,2'S,4a'S,7'R,8a'R)-1-(3-Benzyl-4',4',7'-
trimethyl-octahydro-2H-benzo[e][1,3] oxazin-2'-yl)-2,2,2-trifluoro-1-(4-
methoxyphenyl)ethanol.
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.244(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.602(5)
_cell_length_b                   7.431(3)
_cell_length_c                   14.741(6)
_cell_measurement_temperature    298(2)
_cell_volume                     1260.7(9)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    0.0384
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3621
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.030
_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   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.0823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                2937
_reflns_number_total             3621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052458vsi20060125_090812_1.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021539