Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels-Alder Reactions through Hydrogen Bonding
Aditya K. Unni; Norito Takenaka; Hisashi Yamamoto; Viresh H. Rawal; Journal of the American Chemical Society 127 (2005) 1336–1337; doi:10.1021/ja044076x

data_4111405
_publ_section_title
;
 Axially Chiral Biaryl Diols Catalyze Highly Enantioselective
 Hetero-Diels-Alder Reactions through Hydrogen Bonding
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1336
_journal_page_last               1337
_journal_paper_doi               10.1021/ja044076x
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C53 H40 O3'
_chemical_formula_weight         724.85
_space_group_IT_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                   10.3095(17)
_cell_length_b                   10.4553(18)
_cell_length_c                   35.754(6)
_cell_measurement_temperature    100(2)
_cell_volume                     3853.9(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            37654
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Absorption corrections were applied using SADABS
 based on redundant diffractions. SHELXTL (version 5.1) program library 
 (G. Sheldrick, Bruker Analytical X-ray Systems, Madison, WI).
;
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.160
_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   0.2(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0192P)^2^+1.4065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                6645
_reflns_number_total             6817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja044076xsi20040929_123440.cif
_cod_data_source_block           nori02s
_cod_database_code               4111405