Mn(III)-Mediated Formal [3+3]-Annulation of Vinyl Azides and Cyclopropanols: A Divergent Synthesis of Azaheterocycles
Yi-Feng Wang; Kah Kah Toh; Eileen Pei Jian Ng; Shunsuke Chiba; Journal of the American Chemical Society 133 (2011) 6411–6421; doi:10.1021/ja200879w

data_4106044
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_contact_author_email       shunsuke@ntu.edu.sg
_publ_contact_author_fax         '+65 6791 1961'
_publ_contact_author_phone       '+65 6513 8013'
_publ_section_title
;
 Mn(III)-Mediated Formal [3+3]-Annulation of Vinyl Azides and
 Cyclopropanols: A Divergent Synthesis of Azaheterocycles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6411
_journal_page_last               6421
_journal_paper_doi               10.1021/ja200879w
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C29 H31 N O2'
_chemical_formula_sum            'C29 H31 N O2'
_chemical_formula_weight         425.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 102.997(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.988(2)
_cell_length_b                   7.0092(6)
_cell_length_c                   13.0681(11)
_cell_measurement_reflns_used    4805
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      2.51
_cell_volume                     2230.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7037
_diffrn_reflns_theta_full        31.12
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         7037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.1179
_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^)+(0.1554P)^2^+11.5281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3607
_refine_ls_wR_factor_ref         0.3700
_reflns_number_gt                5781
_reflns_number_total             7037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja200879w_si_004.cif
_cod_data_source_block           21ad_chiba
_cod_database_code               4106044