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_4107219
_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_formula_sum            'C20 H25 F3 O3'
_chemical_formula_weight         370.40
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.556(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2308(17)
_cell_length_b                   13.698(3)
_cell_length_c                   8.5629(18)
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    93
_cell_measurement_theta_max      36.11
_cell_measurement_theta_min      2.38
_cell_volume                     964.5(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker AXS, 2010)'
_computing_data_collection       'Bruker APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'Bruker SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'Brukre SHELXTL (Bruker AXS,2008)'
_computing_publication_material  'Bruker XCIF (Bruker AXS, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11611
_diffrn_reflns_theta_full        35.63
_diffrn_reflns_theta_max         35.63
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       column
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         7559
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0519P)^2^+0.0241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                6685
_reflns_number_total             7559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2085299_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        964.5(3)
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4107219