Diastereoselective Synthesis of Tetrahydrofurans by Lewis Acid Catalyzed Intermolecular Carbenoid-Carbonyl Reaction-Cycloaddition Sequences: Unusual Diastereoselectivity of Lewis Acid Catalyzed Cycloadditions
Yuta Hashimoto; Kennosuke Itoh; Akikazu Kakehi; Motoo Shiro; Hiroyuki Suga; Journal of Organic Chemistry 78 (2013) 6182–6195; doi:10.1021/jo400858u

data_4028369
_publ_section_title
;
 Diastereoselective Synthesis of Tetrahydrofurans by Lewis Acid Catalyzed
 Intermolecular Carbenoid-Carbonyl Reaction-Cycloaddition Sequences:
 Unusual Diastereoselectivity of Lewis Acid Catalyzed Cycloadditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6182
_journal_page_last               6195
_journal_paper_doi               10.1021/jo400858u
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H37 N O6, 0.18(H2 O) '
_chemical_formula_sum            'C30 H37.36 N O6.18'
_chemical_formula_weight         510.87
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   14.9082(3)
_cell_length_b                   18.0949(3)
_cell_length_c                   20.7986(15)
_cell_measurement_reflns_used    31695
_cell_measurement_temperature    153.1
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.2
_cell_volume                     5610.7(4)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            54988
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       block
_exptl_crystal_F_000             2190.40
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  4569 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     694
_refine_ls_number_reflns         10229
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0821P)^2^+2.1239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                8210
_reflns_number_total             10229
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo400858u_si_001.cif
_cod_data_source_block           '_YH-384-B'
_cod_original_formula_sum        'C30 H37.36 N O6.18 '
_cod_database_code               4028369