Diastereoselective Synthesis of β-Heteroaryl syn-α-Methyl-β-Amino Acid Derivatives via a Double Chiral Auxiliary Approach.
Bian, Jianwei; Blakemore, David; Warmus, Joseph S.; Sun, Jianmin; Corbett, Matthew; Rose, Colin R.; Bechle, Bruce M.; Organic letters 15 (2013) 562–565; doi:10.1021/ol3033785

data_1508886
_publ_section_title
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 Diastereoselective Synthesis of \b-Heteroaryl syn-\a-Methyl-\b-Amino Acid
 Derivatives via a Double Chiral Auxiliary Approach.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              562
_journal_page_last               565
_journal_paper_doi               10.1021/ol3033785
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H32 N4 O4 S'
_chemical_formula_weight         472.60
_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                 106.076(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.442(4)
_cell_length_b                   6.2752(18)
_cell_length_c                   16.172(4)
_cell_measurement_reflns_used    1560
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      49.16
_cell_measurement_theta_min      2.84
_cell_volume                     1310.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_sigmaI/netI    0.1077
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4815
_diffrn_reflns_theta_full        50.35
_diffrn_reflns_theta_max         50.35
_diffrn_reflns_theta_min         2.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.382
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_correction_T_min  0.4669
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_coef       0.0033(7)
_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   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         2286
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0775P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1444
_reflns_number_gt                1760
_reflns_number_total             2286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3033785_si_001.cif
_cod_data_source_block           z204
_cod_depositor_comments
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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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1310.7(6)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1508886