Rhodium-catalyzed annulation of ynamides with bifunctional arylboron reagents.
Gourdet, Benoit; Rudkin, Mairi E.; Lam, Hon Wai; Organic letters 12 (2010) 2554–2557; doi:10.1021/ol100769p

data_1502991
_publ_section_title
;
 Rhodium-catalyzed annulation of ynamides with bifunctional arylboron
 reagents.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2554
_journal_page_last               2557
_journal_paper_doi               10.1021/ol100769p
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'Mairi Rudkin'
_chemical_formula_moiety         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 103.311(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   34.5215(10)
_cell_length_b                   6.1850(2)
_cell_length_c                   16.8548(5)
_cell_measurement_reflns_used    4666
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.425
_cell_volume                     3502.08(19)
_computing_cell_refinement       Saint
_computing_data_reduction        Saint
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxs Sheldrick'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'Phi and Omega 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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15129
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.8493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method
'slow diffusion of EtOAc into hexane solution'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0414P)^2^+2.5628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2950
_reflns_number_total             3582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100769p_si_002.cif
_cod_data_source_block           hl9006
_cod_original_cell_volume        3502.08(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1502991