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_4032140
_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_absolute_configuration unk
_chemical_formula_moiety         'C20 H23 N O3 S'
_chemical_formula_sum            'C20 H23 N O3 S'
_chemical_formula_weight         357.45
_chemical_melting_point          393
_chemical_name_systematic
; 
 ? 
;
_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                   6.1952(5)
_cell_length_b                   10.7715(8)
_cell_length_c                   27.987(3)
_cell_measurement_reflns_used    1295
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.9680
_cell_measurement_theta_min      3.7770
_cell_volume                     1867.6(3)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w 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  0.1901
_diffrn_reflns_av_sigmaI/netI    0.1942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            4621
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'face indexing'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.1235
_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^)+(0.0080P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2528
_refine_ls_wR_factor_ref         0.3338
_reflns_number_gt                1608
_reflns_number_total             2920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02260_si_003.cif
_cod_data_source_block           exp_3552
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'UNK' changed to 'unk'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4032139--4032140.cif.
;
_cod_original_sg_symbol_H-M      P_21_21_21
_cod_database_code               4032140