Diastereoselective Synthesis of Enantiopure Morpholines by Electrophilic Selenium-Induced 6-exo Cyclizations on Chiral 3-Allyl-2-hydroxymethylperhydro-1,3-benzoxazine Derivatives
Rafael Pedrosa; Celia Andrés; Pilar Mendiguchía; Javier Nieto; Journal of Organic Chemistry 71 (2006) 8854–8863; doi:10.1021/jo061547k

data_4022083
_publ_section_title
;
 Diastereoselective Synthesis of Enantiopure Morpholines by
 Electrophilic Selenium-Induced 6-exo Cyclizations on Chiral
 3-Allyl-2-hydroxymethylperhydro-1,3-benzoxazine Derivatives
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8854
_journal_page_last               8863
_journal_paper_doi               10.1021/jo061547k
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_sum            'C29 H41 N O2 Se'
_chemical_formula_weight         514.59
_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                   6.777(3)
_cell_length_b                   16.509(7)
_cell_length_c                   24.731(10)
_cell_measurement_temperature    298(2)
_cell_volume                     2767.0(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4005
_diffrn_reflns_theta_full        23.31
_diffrn_reflns_theta_max         23.31
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.796874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.019(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0595
_reflns_number_gt                3178
_reflns_number_total             4005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061547krom20060727_125308.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4022083