Lewis Acid Mediated Asymmetric [2,3]-Sigmatropic Rearrangement of Allylic Amines. Scope and Mechanistic Investigation
Jan Blid; Olaf Panknin; Pavel Tuzina; Peter Somfai; Journal of Organic Chemistry 72 (2007) 1294–1300; doi:10.1021/jo062178v

data_4022693
_publ_contact_author_address
;
Organic Chemistry
School of Chemical Science and Engineering
Royal Institute of Technology (KTH)
100 44 Stockholm
Sweden
;
_publ_contact_author_email       somfai@kth.se
_publ_contact_author_fax         '+46(0)8 791-2333'
_publ_contact_author_name        'Peter Somfai'
_publ_contact_author_phone       '+46(0)8 790-6960'
_publ_section_title
;
 Lewis Acid Mediated Asymmetric [2,3]-Sigmatropic Rearrangement
 of Allylic Amines. Scope and Mechanistic Investigation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1294
_journal_page_last               1300
_journal_paper_doi               10.1021/jo062178v
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C44 H47 B N4 O5 S2, C4 H8 O2'
_chemical_formula_sum            'C48 H55 B N4 O7 S2'
_chemical_formula_weight         874.93
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 110.838(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0143(8)
_cell_length_b                   18.0289(13)
_cell_length_c                   13.7693(12)
_cell_measurement_reflns_used    59
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.7
_cell_measurement_theta_min      5.0
_cell_volume                     2323.4(4)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.085
_diffrn_reflns_av_sigmaI/netI    0.071
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25297
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         4.5
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         8070
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.21
_refine_ls_R_factor_all          0.105
_refine_ls_R_factor_gt           0.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+1.6200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.117
_reflns_number_gt                5744
_reflns_number_total             8070
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo062178vsi20061019_112318.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022693