Diastereoselective Construction of the 6-Oxa-2-azabicyclo[3.2.1]octane Scaffold from Chiral α-Hydroxyaldehyde Derivatives by the Aza-Prins Reaction.
Mahía, Alejandro; Badorrey, Ramón; Gálvez, José A; Díaz-de-Villegas, María D; The Journal of organic chemistry 82 (2017) 8048–8057; doi:10.1021/acs.joc.7b01291

data_4037513
_publ_section_title
;
 Diastereoselective Construction of the 6-Oxa-2-azabicyclo[3.2.1]octane
 Scaffold from Chiral \a-Hydroxyaldehyde Derivatives by the Aza-Prins
 Reaction.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8048
_journal_page_last               8057
_journal_paper_doi               10.1021/acs.joc.7b01291
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H25 N O4 S'
_chemical_formula_sum            'C21 H25 N O4 S'
_chemical_formula_weight         387.48
_chemical_name_systematic
; 
 (1R,5S,7S)-7-[(benzyloxy)methyl]-2-tosyl-6-oxa-2-azabicyclo[3.2.1]octane 
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_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                 112.215(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1421(6)
_cell_length_b                   8.1506(4)
_cell_length_c                   12.8445(8)
_cell_measurement_reflns_used    1198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7696
_cell_measurement_theta_min      3.0239
_cell_volume                     982.97(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device_type  'caliber shapphire3 diffractometer'
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4260
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.83
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.191
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     1
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_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0316P)^2^+0.1847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                2438
_reflns_number_total             2990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01291_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        982.97(10)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037513