Control of Regioselectivity and Stereoselectivity in (4 + 3) Cycloadditions of Chiral Oxyallyls with Unsymmetrically Disubstituted Furans
Yunfei Du; Elizabeth H. Krenske; Jennifer E. Antoline; Andrew G. Lohse; K. N. Houk; Richard P. Hsung; Journal of Organic Chemistry 78 (2013) 1753–1759; doi:10.1021/jo3011792

data_4027972
_publ_section_title
;
 Control of Regioselectivity and Stereoselectivity in (4 + 3)
 Cycloadditions of Chiral Oxyallyls with Unsymmetrically Disubstituted
 Furans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1753
_journal_page_last               1759
_journal_paper_doi               10.1021/jo3011792
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H19 N O6'
_chemical_formula_sum            'C19 H19 N O6'
_chemical_formula_weight         357.35
_chemical_name_common            11197a
_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                 104.137(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0163(9)
_cell_length_b                   8.9386(9)
_cell_length_c                   10.7156(10)
_cell_measurement_reflns_used    2998
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.33
_cell_volume                     837.45(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9672
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9688
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008/4)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.0778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                1855
_reflns_number_total             2045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3011792_si_001.cif
_cod_data_source_block           11197a
_cod_database_code               4027972