Pd-Catalyzed Enantioselective Aerobic Oxidation of Secondary Alcohols: Applications to the Total Synthesis of Alkaloids
Shyam Krishnan; Jeffrey T. Bagdanoff; David C. Ebner; Yeeman K. Ramtohul; Uttam K. Tambar; Brian M. Stoltz; Journal of the American Chemical Society 130 (2008) 13745–13754; doi:10.1021/ja804738b

data_4108474
_publ_section_title
;
 Pd-Catalyzed Enantioselective Aerobic Oxidation of Secondary Alcohols:
 Applications to the Total Synthesis of Alkaloids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13745
_journal_page_last               13754
_journal_paper_doi               10.1021/ja804738b
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C22 H29 N O2'
_chemical_formula_sum            'C22 H29 N O2'
_chemical_formula_weight         339.46
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 107.826(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.1917(12)
_cell_length_b                   8.8565(6)
_cell_length_c                   24.6411(17)
_cell_measurement_reflns_used    4480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.35
_cell_volume                     3779.4(4)
_computing_cell_refinement       'Bruker SAINT v6.45A'
_computing_data_collection       'Bruker SMART v5.630'
_computing_data_reduction        'Bruker SAINT v6.45A'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF v6.12'
_computing_structure_refinement  'Bruker XL v6.12'
_computing_structure_solution    'Bruker XS v6.12'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       '\w scans at 3 \f settings'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25316
_diffrn_reflns_theta_full        26.20
_diffrn_reflns_theta_max         26.20
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
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_exptl_crystal_density_meas      0
_exptl_crystal_description       Needle
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_exptl_crystal_size_max          0.44
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_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    Riding
_refine_ls_matrix_type           'Full matrix'
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.429
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.0814
_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^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                3276
_reflns_number_total             6904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja804738b_si_002.cif
_cod_data_source_block           jtb03
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'direct methods' was changed to
'direct'.

'_atom_sites_solution_secondary' value 'Difference Fourier map' was
changed to 'difmap'.

'_atom_sites_solution_hydrogens' value 'Geometric positions' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               4108474