Diastereoselective Construction of syn-1,3-Dioxanes via a Bismuth-Mediated Two-Component Hemiacetal/Oxa-Conjugate Addition Reaction
P. Andrew Evans; Aleksandr Grisin; Michael J. Lawler; Journal of the American Chemical Society 134 (2012) 2856–2859; doi:10.1021/ja208668u

data_4117451
_publ_section_title
;
 Diastereoselective Construction of syn-1,3-Dioxanes via a
 Bismuth-Mediated Two-Component Hemiacetal/Oxa-Conjugate Addition Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2856
_journal_page_last               2859
_journal_paper_doi               10.1021/ja208668u
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C14 H17 N O5'
_chemical_formula_sum            'C14 H17 N O5'
_chemical_formula_weight         279.29
_chemical_name_common            ag2069
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.429(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.7034(8)
_cell_length_b                   26.890(4)
_cell_length_c                   18.2435(19)
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.69
_cell_measurement_theta_min      2.39
_cell_volume                     2751.7(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2  v2011.2-3 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX detector'
_diffrn_measurement_method       '\w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14747
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_correction_T_min  0.9504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2008/1 (Bruker,2008) was used for absorption correction.
 R(int) was 0.0582 before and 0.0372 after correction.
 The Ratio of minimum to maximum transmission is 0.885.
 The \l/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5858
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0421P)^2^+0.3553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3999
_reflns_number_total             5858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja208668u_si_002.cif
_cod_data_source_block           ag2069m
_cod_database_code               4117451