Diastereoselective synthesis of tetrahydrofurans via reaction of gamma,delta-epoxycarbanions with aldehydes.
Makosza, Mieczysław; Barbasiewicz, Michał; Krajewski, Dariusz; Organic letters 7 (2005) 2945–2948; doi:10.1021/ol0509080

data_1506603
_publ_section_title
;
 Diastereoselective synthesis of tetrahydrofurans via reaction of
 gamma,delta-epoxycarbanions with aldehydes.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2945
_journal_page_last               2948
_journal_paper_doi               10.1021/ol0509080
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C27 H30 O7 S'
_chemical_formula_weight         498.57
_chemical_name_common
;[(2S,4R,5S)-5-phenyl-4-(phenylsulfonyl)
tetrahydro-2-furanyl]methyl (-)-camphanate
;
_chemical_name_systematic
;[(2S,4R,5S)-5-phenyl-4-(phenylsulfonyl)tetrahydro-2-furanyl]
methyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]
heptane-1-carboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   6.0067(4)
_cell_length_b                   11.6597(10)
_cell_length_c                   35.632(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.22
_cell_measurement_theta_min      22.11
_cell_volume                     2495.5(4)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 in WINGX'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            5641
_diffrn_reflns_theta_full        74.21
_diffrn_reflns_theta_max         74.21
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        1.02
_diffrn_standards_interval_count 120
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.530
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.8589
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0702P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1545
_reflns_number_gt                3004
_reflns_number_total             4890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0509080si20050425_032321.cif
_cod_data_source_block           2
_cod_original_cell_volume        2495.6(4)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1506603