An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5 + 2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes
Jian-Jun Feng; Junliang Zhang; Journal of the American Chemical Society 133 (2011) 7304–7307; doi:10.1021/ja2014604

data_4106135
_publ_section_title
;
 An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium
 N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5 + 2]
 Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with
 Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7304
_journal_page_last               7307
_journal_paper_doi               10.1021/ja2014604
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C27 H25 N O3 S'
_chemical_formula_weight         443.54
_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                 96.3830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7395(4)
_cell_length_b                   5.5981(2)
_cell_length_c                   32.0262(11)
_cell_measurement_temperature    296(2)
_cell_volume                     2269.85(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            25139
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0427P)^2^+1.0784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                3016
_reflns_number_total             3989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2014604_si_002.cif
_cod_data_source_block           z
_cod_database_code               4106135