Stereoselective Umpolung Tandem Addition of Heteroatoms to Phenol
Michael A. Todd; Michal Sabat; William H. Myers; Timothy M. Smith; W. Dean Harman; Journal of the American Chemical Society 130 (2008) 6906–6907; doi:10.1021/ja801076z

data_4107854
_publ_section_title
;
 Stereoselective Umpolung Tandem Addition of Heteroatoms to Phenol
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6906
_journal_page_last               6907
_journal_paper_doi               10.1021/ja801076z
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C19 H29 B N7 O4 P W'
_chemical_formula_weight         645.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.223(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2170(10)
_cell_length_b                   13.5450(10)
_cell_length_c                   15.2930(12)
_cell_measurement_reflns_used    5764
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.819
_cell_measurement_theta_min      2.555
_cell_volume                     2389.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22417
_diffrn_reflns_theta_full        36.43
_diffrn_reflns_theta_max         36.43
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    4.942
_exptl_absorpt_correction_T_max  0.812237
_exptl_absorpt_correction_T_min  0.615551
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_description       needle
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.159
_refine_diff_density_min         -1.219
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         11640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                9107
_reflns_number_total             11640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja801076z-file001.cif
_cod_data_source_block           C19H29BN7O4PW
_cod_database_code               4107854