Highly enantioselective oxidative tandem cyclization reaction: a chiral ligand and an anion cooperatively control stereoselectivity
He, Yu-Ping; Wu, Hua; Xu, Lue; Su, Yong-Liang; Gong, Liu-Zhu; Org. Chem. Front. 1 (2014) 473–; doi:10.1039/C4QO00042K

data_1552976
_publ_section_title
;
 Highly enantioselective oxidative tandem cyclization reaction: a chiral
 ligand and an anion cooperatively control stereoselectivity
;
_journal_issue                   5
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              473
_journal_paper_doi               10.1039/C4QO00042K
_journal_volume                  1
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H27 N O'
_chemical_formula_weight         393.51
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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                   10.19460(10)
_cell_length_b                   10.63680(10)
_cell_length_c                   19.86740(10)
_cell_measurement_reflns_used    22446
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.9412
_cell_measurement_theta_min      4.1528
_cell_volume                     2154.38(3)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0085
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30063
_diffrn_reflns_theta_full        71.06
_diffrn_reflns_theta_max         71.06
_diffrn_reflns_theta_min         4.45
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  0.8114
_exptl_absorpt_correction_T_min  0.7870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.1711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                3878
_reflns_number_total             3901
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00042k1.cif
_cod_data_source_block           hyp131118
_cod_database_code               1552976