Scope of Stereoselective Mn-Mediated Radical Addition to Chiral Hydrazones and Application in a Formal Synthesis of Quinine
Gregory K. Friestad; An Ji; Jonas Baltrusaitis; Chandra Sekhar Korapala; Jun Qin; Journal of Organic Chemistry 77 (2012) 3159–3180; doi:10.1021/jo2026349

data_4027103
_publ_section_title
;
 Scope of Stereoselective Mn-Mediated Radical Addition to Chiral
 Hydrazones and Application in a Formal Synthesis of Quinine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3159
_journal_page_last               3180
_journal_paper_doi               10.1021/jo2026349
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C35 H54 O6'
_chemical_formula_sum            'C35 H54 O6'
_chemical_formula_weight         570.78
_chemical_name_systematic
; 
 ? 
;
_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                 100.801(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.5379(13)
_cell_length_b                   10.6801(12)
_cell_length_c                   13.8158(15)
_cell_measurement_reflns_used    7132
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     1672.3(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL v6.1 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL v6.1 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL v6.1 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL v6.1 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega 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  0.0838
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26655
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.1839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                3770
_reflns_number_total             4015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2026349_si_002.cif
_cod_data_source_block           fri61
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_database_code               4027103