Catalytic Asymmetric Synthesis of Stable Oxetenes via Lewis Acid-Promoted [2 + 2] Cycloaddition
Kohsuke Aikawa; Yūta Hioki; Natsumi Shimizu; Koichi Mikami; Journal of the American Chemical Society 133 (2011) 20092–20095; doi:10.1021/ja2085299

data_4107220
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Stable Oxetenes via Lewis Acid-Promoted
 [2 + 2] Cycloaddition
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20092
_journal_page_last               20095
_journal_paper_doi               10.1021/ja2085299
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H28 Cl F3 O7'
_chemical_formula_weight         532.92
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.8129(6)
_cell_length_b                   21.954(2)
_cell_length_c                   40.108(4)
_cell_measurement_reflns_used    752
_cell_measurement_temperature    93.00(10)
_cell_measurement_theta_max      24.3430
_cell_measurement_theta_min      3.6263
_cell_volume                     5118.4(9)
_computing_cell_refinement       'APEX2 v2011.8-RC5 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93.00(10)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            29391
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.274
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       0.00065(15)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     666
_refine_ls_number_reflns         11653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.4795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                8870
_reflns_number_total             11653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2085299_si_003.cif
_cod_data_source_block           I
_cod_database_code               4107220