Diastereoselective Synthesis of Substituted Morpholines from N-Tethered Alkenols: Total Synthesis of (±)-Chelonin A.
Borah, Madhurjya; Borthakur, Upasana; Saikia, Anil K.; The Journal of organic chemistry 82 (2017) 1330–1339; doi:10.1021/acs.joc.6b02260

data_4032139
_publ_section_title
;
 Diastereoselective Synthesis of Substituted Morpholines from N-Tethered
 Alkenols: Total Synthesis of (+-)-Chelonin A.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1330
_journal_page_last               1339
_journal_paper_doi               10.1021/acs.joc.6b02260
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H20 N2 O5 S'
_chemical_formula_sum            'C19 H20 N2 O5 S'
_chemical_formula_weight         388.43
_chemical_melting_point          403
_space_group_IT_number           2
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 92.291(7)
_cell_angle_gamma                90.483(7)
_cell_formula_units_Z            8
_cell_length_a                   8.0238(11)
_cell_length_b                   20.185(3)
_cell_length_c                   24.621(3)
_cell_measurement_reflns_used    6868
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.05
_cell_measurement_theta_min      2.48
_cell_volume                     3958.0(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  0.1020
_diffrn_reflns_av_sigmaI/netI    0.1100
_diffrn_reflns_limit_h_max       9
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_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
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_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            57327
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         0.83
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'face indexing'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1630
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     977
_refine_ls_number_reflns         13346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.262
_refine_ls_R_factor_all          0.1946
_refine_ls_R_factor_gt           0.1468
_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^)+(0.0100P)^2^+20.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3316
_refine_ls_wR_factor_ref         0.3527
_reflns_number_gt                7984
_reflns_number_total             13346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02260_si_004.cif
_cod_data_source_block           mb-nitro_0m
_cod_depositor_comments
'Adding full bibliography for 4032139--4032140.cif.'
_cod_original_cell_volume        3957.9(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4032139