Organoselenium-catalyzed, hydroxy-controlled regio- and stereoselective amination of terminal alkenes: efficient synthesis of 3-amino allylic alcohols.
Deng, Zhimin; Wei, Jialiang; Liao, Lihao; Huang, Haiyan; Zhao, Xiaodan; Organic letters 17 (2015) 1834–1837; doi:10.1021/acs.orglett.5b00213

data_1554809
_publ_section_title
;
 Organoselenium-catalyzed, hydroxy-controlled regio- and stereoselective
 amination of terminal alkenes: efficient synthesis of 3-amino allylic
 alcohols.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1834
_journal_page_last               1837
_journal_paper_doi               10.1021/acs.orglett.5b00213
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C19 H18 N O5 S2'
_chemical_formula_sum            'C19 H18 N O5 S2'
_chemical_formula_weight         404.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                98.477(4)
_cell_angle_beta                 91.135(4)
_cell_angle_gamma                97.754(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9459(4)
_cell_length_b                   8.3713(5)
_cell_length_c                   15.0845(6)
_cell_measurement_reflns_used    2627
_cell_measurement_temperature    293.35(10)
_cell_measurement_theta_max      27.8190
_cell_measurement_theta_min      3.4100
_cell_volume                     982.54(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.35(10)
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.9928
_diffrn_measured_fraction_theta_max 0.9928
_diffrn_measurement_details
;
  1 omega   -4.00   72.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4312  -99.0000  -30.0000 76

  2 omega -109.00  -42.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5093 -179.0000  120.0000 67

  3 omega   13.00   52.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5093   37.0000  150.0000 39

  4 omega  -95.00   56.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5093   19.0000  120.0000 151

  5 omega -110.00  -74.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5093 -179.0000    0.0000 36
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0894945000
_diffrn_orient_matrix_UB_12      -0.0027040000
_diffrn_orient_matrix_UB_13      -0.0037724000
_diffrn_orient_matrix_UB_21      0.0100735000
_diffrn_orient_matrix_UB_22      0.0862909000
_diffrn_orient_matrix_UB_23      0.0040779000
_diffrn_orient_matrix_UB_31      0.0043362000
_diffrn_orient_matrix_UB_32      -0.0055339000
_diffrn_orient_matrix_UB_33      -0.0472546000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6194
_diffrn_reflns_theta_full        25.9998
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3671
_exptl_crystal_description       block
_exptl_crystal_F_000             422.7083
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.5708
_refine_diff_density_min         -0.3686
_refine_diff_density_rms         0.0779
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             7.0768
_refine_ls_goodness_of_fit_ref   1.0710
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0710
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.6450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3181
_reflns_number_total             3842
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol5b00213_si_003.cif
_cod_data_source_block           exp_19725
_cod_database_code               1554809
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O7(0.5) C44(0.5) O6(0.5) C41(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C21(H21a,H21b)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C30(H30a,H30b,H30c)
;
_olex2_submission_special_instructions 'No special instructions were received'