Catalytic Asymmetric Synthesis of a Tertiary Benzylic Carbon Center via Phenol-Directed Alkene Hydrogenation
Seb Caille; Rich Crockett; Krishnakumar Ranganathan; Xiang Wang; Jacqueline C. S. Woo; Shawn D. Walker; Journal of Organic Chemistry 76 (2011) 5198–5206; doi:10.1021/jo200941r

data_4026448
_publ_section_title
;
 Catalytic Asymmetric Synthesis of a Tertiary Benzylic Carbon Center via
 Phenol-Directed Alkene Hydrogenation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5198
_journal_page_last               5206
_journal_paper_doi               10.1021/jo200941r
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H27 N O3'
_chemical_formula_sum            'C23 H27 N O3'
_chemical_formula_weight         365.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.24080(10)
_cell_length_b                   8.32250(10)
_cell_length_c                   34.4966(5)
_cell_measurement_reflns_used    4961
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.53
_cell_measurement_theta_min      5.13
_cell_volume                     2078.82(5)
_computing_cell_refinement       'APEX2 (BRUKER, V5-0, 2008)'
_computing_data_collection       'COSMO (BRUKER, V1.58, 2007)'
_computing_data_reduction        'SAINT (BRUKER, V7.56A, 2008)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            8198
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         68.05
_diffrn_reflns_theta_min         2.56
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_correction_T_min  0.7050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       needle_plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.0927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                3363
_reflns_number_total             3605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200941r_si_001.cif
_cod_data_source_block           amg2308_0m
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_database_code               4026448