Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the Iron-Catalyzed Stereoselective Olefin Diazidation.
Li, Hongze; Shen, Shou-Jie; Zhu, Cheng-Liang; Xu, Hao; Journal of the American Chemical Society 140 (2018) 10619–10626; doi:10.1021/jacs.8b06900

data_4132836
_publ_section_title
;
 Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the
 Iron-Catalyzed Stereoselective Olefin Diazidation.
;
_journal_issue                   33
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10619
_journal_page_last               10626
_journal_paper_doi               10.1021/jacs.8b06900
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C11 H15 N7 O6'
_chemical_formula_sum            'C11 H15 N7 O6'
_chemical_formula_weight         341.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-31
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0517(2)
_cell_length_b                   8.04410(10)
_cell_length_c                   24.0949(3)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.11
_cell_measurement_theta_min      5.56
_cell_volume                     3049.85(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20954
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.100
_diffrn_reflns_theta_min         3.743
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.7117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0435 before and 0.0374 after correction. The Ratio of minimum to maximum transmission is 0.9444. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             1424
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.344
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+2.1715P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2846
_reflns_number_total             2936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b06900_si_002.cif
_cod_data_source_block           hx118a
_cod_database_code               4132836
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.712
_shelx_estimated_absorpt_t_min   0.676
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id HL-DAP
_olex2_submission_special_instructions 'No special instructions were received'