Enantioselective Synthesis of Dihydropyrazoles by Formal [4+1] Cycloaddition of in Situ-Derived Azoalkenes and Sulfur Ylides
Jia-Rong Chen; Wan-Rong Dong; Mathieu Candy; Fang-Fang Pan; Manuel Jörres; Carsten Bolm; Journal of the American Chemical Society 134 (2012) 6924–6927; doi:10.1021/ja301196x

data_4117853
_publ_contact_author_address
;
      Institut fuer Organische Chemie
      RWTH Aachen
      Landoltweg 1
      52074 Aachen
      Germany
;
_publ_contact_author_name        'Carsten Bolm'
_publ_section_title
;
 Enantioselective Synthesis of Dihydropyrazoles by Formal [4+1]
 Cycloaddition of in Situ-Derived Azoalkenes and Sulfur Ylides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6924
_journal_page_last               6927
_journal_paper_doi               10.1021/ja301196x
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H17 Br N2 O2'
_chemical_formula_sum            'C23 H17 Br N2 O2'
_chemical_formula_weight         433.30
_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                   8.694(2)
_cell_length_b                   12.552(3)
_cell_length_c                   17.328(4)
_cell_measurement_reflns_used    5032
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.1061
_cell_measurement_theta_min      2.6235
_cell_volume                     1891.0(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker,2001)'
_computing_data_reduction        'SAINT (Bruker,1999)'
_computing_molecular_graphics    'PLATON (Spek,2003)'
_computing_publication_material  'SHELXL-97 (sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23564
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    2.196
_exptl_absorpt_correction_T_max  0.6321
_exptl_absorpt_correction_T_min  0.5588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       brick
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.3848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0652
_reflns_number_gt                3976
_reflns_number_total             4295
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja301196x_si_001.cif
_cod_data_source_block           osad
_cod_original_cell_volume        1891.0(7)
_cod_database_code               4117853