Catalytic Enantioselective Allylic Amination of Unactivated Terminal Olefins via an Ene Reaction/[2,3]-Rearrangement
Hongli Bao; Uttam K. Tambar; Journal of the American Chemical Society 134 (2012) 18495–18498; doi:10.1021/ja307851b

data_4118883
_publ_section_title
;
 Catalytic Enantioselective Allylic Amination of Unactivated Terminal
 Olefins via an Ene Reaction/[2,3]-Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18495
_journal_page_last               18498
_journal_paper_doi               10.1021/ja307851b
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H26 N2 O4 S3'
_chemical_formula_weight         466.62
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.556(4)
_cell_angle_beta                 73.339(5)
_cell_angle_gamma                66.602(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7151(7)
_cell_length_b                   10.1879(11)
_cell_length_c                   14.983(2)
_cell_measurement_reflns_used    16038
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      74.0
_cell_measurement_theta_min      7.0
_cell_volume                     1159.0(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Rigaku R-Axis Spider with Image Plate'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15894
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         7.04
_exptl_absorpt_coefficient_mu    3.171
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       prisms
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7001
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0530P)^2^+0.3497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                5729
_reflns_number_total             7001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja307851b_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4118883